NL1012300C2 - Stabilisator voor farmaca. - Google Patents

Stabilisator voor farmaca. Download PDF

Info

Publication number: NL1012300C2
Authority: NL; Netherlands
Prior art keywords: inulin; pharmacon; fructan; sugar; glass
Prior art date: 1999-06-11

Application number

NL1012300A

Other languages

English (en)

Dutch (nl)

Inventor

Hendrik Willem Frijlink

Wouter Leonardus Jose Hinrichs

Original Assignee

Rijksuniversiteit

Priority date (The priority date 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 date listed.)

1999-06-11

Filing date

1999-06-11

Publication date

2000-12-12

1999-06-11 Application filed by Rijksuniversiteit filed Critical Rijksuniversiteit

1999-06-11 Priority to NL1012300A priority Critical patent/NL1012300C2/nl

2000-06-13 Priority to DE60001744T priority patent/DE60001744T2/de

2000-06-13 Priority to PCT/NL2000/000405 priority patent/WO2000078817A1/en

2000-06-13 Priority to CA002375241A priority patent/CA2375241C/en

2000-06-13 Priority to AT00941031T priority patent/ATE234868T1/de

2000-06-13 Priority to AU55797/00A priority patent/AU5579700A/en

2000-06-13 Priority to EP00941031A priority patent/EP1194453B1/de

2000-12-12 Application granted granted Critical

2000-12-12 Publication of NL1012300C2 publication Critical patent/NL1012300C2/nl

2001-12-07 Priority to US10/007,800 priority patent/US6841169B2/en

Links

239000003814 drug Substances 0.000 title claims abstract description 45
239000003381 stabilizer Substances 0.000 title claims description 7
235000000346 sugar Nutrition 0.000 claims abstract description 39
229920002670 Fructan Polymers 0.000 claims abstract description 38
239000011521 glass Substances 0.000 claims abstract description 33
239000013543 active substance Substances 0.000 claims abstract description 15
230000000087 stabilizing effect Effects 0.000 claims abstract description 7
229920001202 Inulin Polymers 0.000 claims description 41
JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 claims description 40
229940029339 inulin Drugs 0.000 claims description 40
238000000034 method Methods 0.000 claims description 12
238000001694 spray drying Methods 0.000 claims description 7
230000002685 pulmonary effect Effects 0.000 claims description 6
-1 dermatic Substances 0.000 claims description 5
239000003826 tablet Substances 0.000 claims description 5
239000000829 suppository Substances 0.000 claims description 4
238000001291 vacuum drying Methods 0.000 claims description 4
239000002775 capsule Substances 0.000 claims description 3
239000007937 lozenge Substances 0.000 claims description 3
239000000843 powder Substances 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims 2
238000007918 intramuscular administration Methods 0.000 claims 1
238000007920 subcutaneous administration Methods 0.000 claims 1
238000009777 vacuum freeze-drying Methods 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 10
238000006116 polymerization reaction Methods 0.000 abstract description 5
239000000825 pharmaceutical preparation Substances 0.000 abstract 1
239000000243 solution Substances 0.000 description 23
ZFTFOHBYVDOAMH-XNOIKFDKSA-N (2r,3s,4s,5r)-5-[[(2r,3s,4s,5r)-5-[[(2r,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]oxymethyl]-2-(hydroxymethyl)oxolane-2,3,4-triol Chemical class O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(OC[C@@H]2[C@H]([C@H](O)[C@@](O)(CO)O2)O)O1 ZFTFOHBYVDOAMH-XNOIKFDKSA-N 0.000 description 22
229940079593 drug Drugs 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
238000002425 crystallisation Methods 0.000 description 14
230000008025 crystallization Effects 0.000 description 14
102000004169 proteins and genes Human genes 0.000 description 14
108090000623 proteins and genes Proteins 0.000 description 14
108090000765 processed proteins & peptides Proteins 0.000 description 13
HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 9
HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 9
HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 9
238000001035 drying Methods 0.000 description 9
102000004196 processed proteins & peptides Human genes 0.000 description 9
150000008163 sugars Chemical class 0.000 description 8
239000002671 adjuvant Substances 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
238000004108 freeze drying Methods 0.000 description 5
230000001965 increasing effect Effects 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
230000009477 glass transition Effects 0.000 description 4
150000004676 glycans Chemical class 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
229920001282 polysaccharide Polymers 0.000 description 4
239000005017 polysaccharide Substances 0.000 description 4
230000008569 process Effects 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
102000002260 Alkaline Phosphatase Human genes 0.000 description 3
108020004774 Alkaline Phosphatase Proteins 0.000 description 3
241000723343 Cichorium Species 0.000 description 3
235000007542 Cichorium intybus Nutrition 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000007983 Tris buffer Substances 0.000 description 3
125000003172 aldehyde group Chemical group 0.000 description 3
230000008901 benefit Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
230000007246 mechanism Effects 0.000 description 3
150000002482 oligosaccharides Polymers 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000000859 sublimation Methods 0.000 description 3
230000008022 sublimation Effects 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
244000115658 Dahlia pinnata Species 0.000 description 2
235000012040 Dahlia pinnata Nutrition 0.000 description 2
241000792859 Enema Species 0.000 description 2
240000008892 Helianthus tuberosus Species 0.000 description 2
235000003230 Helianthus tuberosus Nutrition 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000004925 denaturation Methods 0.000 description 2
230000036425 denaturation Effects 0.000 description 2
239000007920 enema Substances 0.000 description 2
229940079360 enema for constipation Drugs 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000008014 freezing Effects 0.000 description 2
238000007710 freezing Methods 0.000 description 2
BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000003993 interaction Effects 0.000 description 2
239000007927 intramuscular injection Substances 0.000 description 2
238000010255 intramuscular injection Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
150000002772 monosaccharides Chemical class 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
229920001542 oligosaccharide Polymers 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000002245 particle Substances 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000007929 subcutaneous injection Substances 0.000 description 2
238000010254 subcutaneous injection Methods 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000208838 Asteraceae Species 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229920001503 Glucan Polymers 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000234280 Liliaceae Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical group OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000001010 compromised effect Effects 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
230000009615 deamination Effects 0.000 description 1
238000006481 deamination reaction Methods 0.000 description 1
230000006735 deficit Effects 0.000 description 1
230000003412 degenerative effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
150000002016 disaccharides Chemical class 0.000 description 1
238000009826 distribution Methods 0.000 description 1
125000002228 disulfide group Chemical group 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000007210 heterogeneous catalysis Methods 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000006207 intravenous dosage form Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
AIHDCSAXVMAMJH-GFBKWZILSA-N levan Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(CO[C@@H]2[C@H]([C@H](O)[C@@](O)(CO)O2)O)O1 AIHDCSAXVMAMJH-GFBKWZILSA-N 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
238000005374 membrane filtration Methods 0.000 description 1
239000003595 mist Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000000465 moulding Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000000700 radioactive tracer Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000004904 shortening Methods 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000012798 spherical particle Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 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
239000011782 vitamin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/10—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a carbohydrate
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0051—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Fructofuranans, e.g. beta-2,6-D-fructofuranan, i.e. levan; Derivatives thereof
- C08B37/0054—Inulin, i.e. beta-2,1-D-fructofuranan; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/96—Stabilising an enzyme by forming an adduct or a composition; Forming enzyme conjugates

Landscapes

Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Organic Chemistry (AREA)
Zoology (AREA)
Bioinformatics & Cheminformatics (AREA)
Wood Science & Technology (AREA)
Genetics & Genomics (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Biomedical Technology (AREA)
Medicinal Chemistry (AREA)
Microbiology (AREA)
General Engineering & Computer Science (AREA)
Polymers & Plastics (AREA)
Chemical Kinetics & Catalysis (AREA)
Materials Engineering (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NL1012300A 1999-06-11 1999-06-11 Stabilisator voor farmaca. NL1012300C2 (nl)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
NL1012300A NL1012300C2 (nl)	1999-06-11	1999-06-11	Stabilisator voor farmaca.
DE60001744T DE60001744T2 (de)	1999-06-11	2000-06-13	Stabilisator für arzneimittel
PCT/NL2000/000405 WO2000078817A1 (en)	1999-06-11	2000-06-13	Stabilizer for pharmacons
CA002375241A CA2375241C (en)	1999-06-11	2000-06-13	Stabilizer for pharmacons
AT00941031T ATE234868T1 (de)	1999-06-11	2000-06-13	Stabilisator für arzneimittel
AU55797/00A AU5579700A (en)	1999-06-11	2000-06-13	Stabilizer for pharmacons
EP00941031A EP1194453B1 (de)	1999-06-11	2000-06-13	Stabilisator für arzneimittel
US10/007,800 US6841169B2 (en)	1999-06-11	2001-12-07	Stabilizer for pharmacons

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL1012300A NL1012300C2 (nl)	1999-06-11	1999-06-11	Stabilisator voor farmaca.
NL1012300		1999-06-11

Publications (1)

Publication Number	Publication Date
NL1012300C2 true NL1012300C2 (nl)	2000-12-12

Family

ID=19769360

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1012300A NL1012300C2 (nl)	1999-06-11	1999-06-11	Stabilisator voor farmaca.

Country Status (8)

Country	Link
US (1)	US6841169B2 (de)
EP (1)	EP1194453B1 (de)
AT (1)	ATE234868T1 (de)
AU (1)	AU5579700A (de)
CA (1)	CA2375241C (de)
DE (1)	DE60001744T2 (de)
NL (1)	NL1012300C2 (de)
WO (1)	WO2000078817A1 (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10026698A1 (de)	2000-05-30	2001-12-06	Basf Ag	Selbstemulgierende Wirkstoffformulierung und Verwendung dieser Formulierung
US7209304B2 (en) *	2001-06-29	2007-04-24	Seagate Technology Llc	Systems, apparatus, and methods to determine thermal decay characterization from an equalized signal-to-noise ratio of a magnetic disc drive device
PL209134B1 (pl) *	2002-04-03	2011-07-29	Solvay Pharm Bv	Sposób wytwarzania kompozycji farmaceutycznej zawierającej naturalny związek kanabinoidowy i kompozycja farmaceutyczna otrzymywana tym sposobem
EP1428526A1 (de) *	2002-12-13	2004-06-16	Rijksuniversiteit Groningen	Zusammensetzung zur schnellen Freisetzung von lipophilen Stoffen
US8377952B2 (en)	2003-08-28	2013-02-19	Abbott Laboratories	Solid pharmaceutical dosage formulation
US8025899B2 (en)	2003-08-28	2011-09-27	Abbott Laboratories	Solid pharmaceutical dosage form
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Also Published As

Publication number	Publication date
DE60001744T2 (de)	2004-03-18
WO2000078817A1 (en)	2000-12-28
EP1194453B1 (de)	2003-03-19
CA2375241C (en)	2009-12-22
CA2375241A1 (en)	2000-12-28
US6841169B2 (en)	2005-01-11
US20020122825A1 (en)	2002-09-05
ATE234868T1 (de)	2003-04-15
DE60001744D1 (de)	2003-04-24
EP1194453A1 (de)	2002-04-10
AU5579700A (en)	2001-01-09

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