DE69815659T2 - Zusammensetzung zur kontrollierten freisetzung - Google Patents
Zusammensetzung zur kontrollierten freisetzung Download PDFInfo
- Publication number
- DE69815659T2 DE69815659T2 DE69815659T DE69815659T DE69815659T2 DE 69815659 T2 DE69815659 T2 DE 69815659T2 DE 69815659 T DE69815659 T DE 69815659T DE 69815659 T DE69815659 T DE 69815659T DE 69815659 T2 DE69815659 T2 DE 69815659T2
- Authority
- DE
- Germany
- Prior art keywords
- composition
- weight
- composition according
- phase
- liquid
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 238000013270 controlled release Methods 0.000 title claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 51
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000011149 active material Substances 0.000 claims abstract description 24
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 55
- 239000000194 fatty acid Substances 0.000 claims description 55
- 229930195729 fatty acid Natural products 0.000 claims description 55
- 150000004665 fatty acids Chemical class 0.000 claims description 51
- -1 diglycerol ester Chemical class 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 150000002632 lipids Chemical class 0.000 claims description 19
- 238000009472 formulation Methods 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 9
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 8
- 230000007704 transition Effects 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 235000011187 glycerol Nutrition 0.000 claims description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 4
- 239000005642 Oleic acid Substances 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 150000004668 long chain fatty acids Chemical class 0.000 claims description 3
- 150000004667 medium chain fatty acids Chemical class 0.000 claims description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 3
- 235000021313 oleic acid Nutrition 0.000 claims description 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 3
- 239000005639 Lauric acid Substances 0.000 claims description 2
- 235000004443 Ricinus communis Nutrition 0.000 claims description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- 239000012567 medical material Substances 0.000 claims description 2
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 2
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 2
- 229940088623 biologically active substance Drugs 0.000 claims 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 239000008206 lipophilic material Substances 0.000 claims 1
- 239000012669 liquid formulation Substances 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 150000002646 long chain fatty acid esters Chemical class 0.000 abstract 1
- 150000002711 medium chain fatty acid esters Chemical class 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 58
- 150000002148 esters Chemical class 0.000 description 15
- 229940105990 diglycerin Drugs 0.000 description 14
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 7
- 229930105110 Cyclosporin A Natural products 0.000 description 7
- 108010036949 Cyclosporine Proteins 0.000 description 7
- 229960001265 ciclosporin Drugs 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920000223 polyglycerol Polymers 0.000 description 6
- OEMYNKBAVGXYQR-XXAVUKJNSA-N (z)-octadec-9-enoic acid;propane-1,2,3-triol Chemical class OCC(O)CO.OCC(O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O OEMYNKBAVGXYQR-XXAVUKJNSA-N 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- MLSVJHOYXJGGTR-IFHOVBQLSA-N acetic acid;(2s)-n-[(2r)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-1-[(4r,7s,10s,13s,16s)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,1 Chemical compound CC(O)=O.C([C@H]1C(=O)N[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSCCC(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](CCCNC(N)=N)C(=O)NCC(N)=O)=O)CCC(=O)N)C1=CC=CC=C1 MLSVJHOYXJGGTR-IFHOVBQLSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000010587 phase diagram Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000227 bioadhesive Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 229930182912 cyclosporin Natural products 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 239000000186 progesterone Substances 0.000 description 2
- 229960003387 progesterone Drugs 0.000 description 2
- 238000000526 short-path distillation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- PHDVPEOLXYBNJY-KTKRTIGZSA-N 2-(2-hydroxyethoxy)ethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCOCCO PHDVPEOLXYBNJY-KTKRTIGZSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005267 amalgamation Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000035587 bioadhesion Effects 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1274—Non-vesicle bilayer structures, e.g. liquid crystals, tubules, cubic phases or cochleates; Sponge phases
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9700061A SE511313C2 (sv) | 1997-01-13 | 1997-01-13 | Komposition med reglerad frisättning innefattande fettsyraester av diacylglycerol |
| SE9700061 | 1997-01-13 | ||
| PCT/SE1998/000009 WO1998030206A1 (en) | 1997-01-13 | 1998-01-08 | Controlled release composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69815659D1 DE69815659D1 (de) | 2003-07-24 |
| DE69815659T2 true DE69815659T2 (de) | 2004-04-29 |
Family
ID=20405393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69815659T Expired - Lifetime DE69815659T2 (de) | 1997-01-13 | 1998-01-08 | Zusammensetzung zur kontrollierten freisetzung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6660278B1 (https=) |
| EP (1) | EP0954287B1 (https=) |
| JP (1) | JP2001508773A (https=) |
| AT (1) | ATE243024T1 (https=) |
| AU (1) | AU5583298A (https=) |
| CA (1) | CA2277377C (https=) |
| DE (1) | DE69815659T2 (https=) |
| SE (1) | SE511313C2 (https=) |
| WO (1) | WO1998030206A1 (https=) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020153508A1 (en) | 2000-06-29 | 2002-10-24 | Lynch Matthew Lawrence | Cubic liquid crystalline compositions and methods for their preparation |
| US6946137B2 (en) * | 2001-10-19 | 2005-09-20 | Idexx Laboratories, Inc. | Methods for the controlled delivery of pharmacologically active compounds |
| WO2003034988A2 (en) | 2001-10-19 | 2003-05-01 | Idexx Laboratories, Inc. | Injectable compositions for the controlled delivery of pharmacologically active compound |
| US7439268B2 (en) * | 2003-07-18 | 2008-10-21 | Idexx Laboratories | Compositions containing prodrugs of florfenicol and methods of use |
| US20050049210A1 (en) * | 2003-08-27 | 2005-03-03 | Idexx Laboratories, Inc. | Methods for the controlled delivery of pharmacologically active compounds |
| US8236292B2 (en) * | 2004-06-04 | 2012-08-07 | Camurus Ab | Liquid depot formulations |
| US9592324B2 (en) | 2006-11-06 | 2017-03-14 | Atrium Medical Corporation | Tissue separating device with reinforced support for anchoring mechanisms |
| EP1811935B1 (en) | 2004-09-28 | 2016-03-30 | Atrium Medical Corporation | Heat cured gel and method of making |
| US9801982B2 (en) | 2004-09-28 | 2017-10-31 | Atrium Medical Corporation | Implantable barrier device |
| US9000040B2 (en) | 2004-09-28 | 2015-04-07 | Atrium Medical Corporation | Cross-linked fatty acid-based biomaterials |
| US20060067977A1 (en) | 2004-09-28 | 2006-03-30 | Atrium Medical Corporation | Pre-dried drug delivery coating for use with a stent |
| US9012506B2 (en) | 2004-09-28 | 2015-04-21 | Atrium Medical Corporation | Cross-linked fatty acid-based biomaterials |
| US20070059350A1 (en) * | 2004-12-13 | 2007-03-15 | Kennedy John P | Agents for controlling biological fluids and methods of use thereof |
| US20060127437A1 (en) * | 2004-12-13 | 2006-06-15 | Misty Anderson Kennedy | Semisolid system and combination semisolid, multiparticulate system for sealing tissues and/or controlling biological fluids |
| US8535709B2 (en) * | 2004-12-13 | 2013-09-17 | Southeastern Medical Technologies, Llc | Agents for controlling biological fluids and methods of use thereof |
| US8288348B2 (en) * | 2005-07-13 | 2012-10-16 | Allergan, Inc. | Cyclosporin compositions |
| US9427423B2 (en) | 2009-03-10 | 2016-08-30 | Atrium Medical Corporation | Fatty-acid based particles |
| US9278161B2 (en) | 2005-09-28 | 2016-03-08 | Atrium Medical Corporation | Tissue-separating fatty acid adhesion barrier |
| AU2006304590A1 (en) | 2005-10-15 | 2007-04-26 | Atrium Medical Corporation | Hydrophobic cross-linked gels for bioabsorbable drug carrier coatings |
| US9492596B2 (en) | 2006-11-06 | 2016-11-15 | Atrium Medical Corporation | Barrier layer with underlying medical device and one or more reinforcing support structures |
| US7550625B2 (en) * | 2007-10-19 | 2009-06-23 | Idexx Laboratories | Esters of florfenicol |
| US8603999B2 (en) | 2008-12-05 | 2013-12-10 | Commonwealth Scientific And Industrial Research Organisation | Amphiphile prodrugs |
| US20110038910A1 (en) | 2009-08-11 | 2011-02-17 | Atrium Medical Corporation | Anti-infective antimicrobial-containing biomaterials |
| WO2011050388A1 (en) * | 2009-10-30 | 2011-05-05 | Monash University | Liquid crystal composition and method of use |
| KR101663551B1 (ko) * | 2010-05-18 | 2016-10-07 | 후지필름 가부시키가이샤 | 카로티노이드 함유 조성물 및 그 제조 방법 |
| US10322213B2 (en) | 2010-07-16 | 2019-06-18 | Atrium Medical Corporation | Compositions and methods for altering the rate of hydrolysis of cured oil-based materials |
| US9867880B2 (en) | 2012-06-13 | 2018-01-16 | Atrium Medical Corporation | Cured oil-hydrogel biomaterial compositions for controlled drug delivery |
| HRP20210068T1 (hr) | 2012-07-26 | 2021-03-05 | Camurus Ab | Opioidne formulacije |
| WO2014016428A1 (en) | 2012-07-26 | 2014-01-30 | Camurus Ab | Opioid formulations |
| EP3716954A1 (en) | 2017-11-27 | 2020-10-07 | Umecrine Cognition AB | Pharmaceutical formulation of 3 -ethynyl-3 -hydroxyandrostan-17-one oxime |
| AU2019258590B2 (en) | 2018-04-26 | 2022-09-08 | NanoMed Holdings Pty Ltd | Gemcitabine amphiphile prodrugs |
| EP3810622A4 (en) | 2018-06-21 | 2022-04-06 | NanoMed Holdings Pty Ltd | PLATINUM BASED AMPHIPHILIC PRODRUGS |
| CN116867376A (zh) * | 2021-01-29 | 2023-10-10 | Ioi油脂化学品有限责任公司 | 含有聚甘油脂肪酸酯的组合物 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5321393B2 (https=) * | 1974-10-19 | 1978-07-03 | ||
| US5264460A (en) * | 1988-05-30 | 1993-11-23 | Deutsche Solvay-Werke Gmbh | Process for preparing nonionic surfactants |
| KR0148748B1 (ko) | 1988-09-16 | 1998-08-17 | 장 크라메르, 한스 루돌프 하우스 | 사이클로스포린을 함유하는 약학조성물 |
| IE65045B1 (en) | 1990-04-28 | 1995-10-04 | Takeda Chemical Industries Ltd | Granulated preparations and method of producing the same |
| AU668509B2 (en) * | 1991-04-19 | 1996-05-09 | Affinity Biotech, Inc. | Convertible microemulsion formulations |
| SE518578C2 (sv) * | 1994-06-15 | 2002-10-29 | Gs Dev Ab | Lipidbaserad komposition |
| US6013269A (en) * | 1994-10-12 | 2000-01-11 | The Procter & Gamble Company | Cosmetic make-up compositions |
| SE504582C2 (sv) | 1995-07-06 | 1997-03-10 | Gs Dev Ab | Cyklosporinkomposition baserad på en L2-fas |
| CZ288739B6 (cs) * | 1996-08-01 | 2001-08-15 | Galena, A. S. | Cyklosporin obsahující léčivé přípravky |
-
1997
- 1997-01-13 SE SE9700061A patent/SE511313C2/sv not_active IP Right Cessation
-
1998
- 1998-01-08 US US09/341,294 patent/US6660278B1/en not_active Expired - Fee Related
- 1998-01-08 WO PCT/SE1998/000009 patent/WO1998030206A1/en not_active Ceased
- 1998-01-08 AU AU55832/98A patent/AU5583298A/en not_active Abandoned
- 1998-01-08 CA CA002277377A patent/CA2277377C/en not_active Expired - Fee Related
- 1998-01-08 JP JP53080298A patent/JP2001508773A/ja not_active Ceased
- 1998-01-08 EP EP98900793A patent/EP0954287B1/en not_active Expired - Lifetime
- 1998-01-08 DE DE69815659T patent/DE69815659T2/de not_active Expired - Lifetime
- 1998-01-08 AT AT98900793T patent/ATE243024T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998030206A1 (en) | 1998-07-16 |
| US6660278B1 (en) | 2003-12-09 |
| DE69815659D1 (de) | 2003-07-24 |
| EP0954287A1 (en) | 1999-11-10 |
| SE511313C2 (sv) | 1999-09-06 |
| CA2277377C (en) | 2007-12-18 |
| ATE243024T1 (de) | 2003-07-15 |
| EP0954287B1 (en) | 2003-06-18 |
| CA2277377A1 (en) | 1998-07-16 |
| SE9700061L (sv) | 1998-07-14 |
| AU5583298A (en) | 1998-08-03 |
| JP2001508773A (ja) | 2001-07-03 |
| SE9700061D0 (sv) | 1997-01-13 |
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