NO319049B1 - Hurtigopplosende farmasoytisk preparat som omfatter mikronisert (R)-2-(4-brom-2-fluorbenzyl)-1,2,3,4-tetrahydropyrrol[1,2-a]pyrazin-4-spiro-3'-pyrrolidin-1,2',3,5'-tetron - Google Patents

Hurtigopplosende farmasoytisk preparat som omfatter mikronisert (R)-2-(4-brom-2-fluorbenzyl)-1,2,3,4-tetrahydropyrrol[1,2-a]pyrazin-4-spiro-3'-pyrrolidin-1,2',3,5'-tetron Download PDF

Info

Publication number: NO319049B1
Authority: NO; Norway
Prior art keywords: weight; ratio; pharmaceutical preparation; fast; micronized
Prior art date: 1997-10-20

Application number

NO20002049A

Other languages

English (en)

Norwegian (no)

Other versions

NO20002049D0 (no

NO20002049L (no

Inventor

Mamoru Ohashi

Kazuyoshi Ogasawara

Yoshimi Shirai

Hiroshi Fujioka

Original Assignee

Dainippon Pharmaceutical Co

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.)

1997-10-20

Filing date

2000-04-18

Publication date

2005-06-06

2000-04-18 Application filed by Dainippon Pharmaceutical Co filed Critical Dainippon Pharmaceutical Co

2000-04-18 Publication of NO20002049D0 publication Critical patent/NO20002049D0/no

2000-06-19 Publication of NO20002049L publication Critical patent/NO20002049L/no

2005-06-06 Publication of NO319049B1 publication Critical patent/NO319049B1/no

Links

239000008194 pharmaceutical composition Substances 0.000 title abstract 3
-1 (R) -2- (4-bromo-2-fluorobenzyl) -1,2,3,4-tetrahydropyrrole Chemical compound 0.000 title description 3
238000004090 dissolution Methods 0.000 claims abstract description 21
239000000825 pharmaceutical preparation Substances 0.000 claims description 35
239000002245 particle Substances 0.000 claims description 19
239000013543 active substance Substances 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
230000002378 acidificating effect Effects 0.000 claims description 11
238000007922 dissolution test Methods 0.000 claims description 11
239000011230 binding agent Substances 0.000 claims description 10
239000000314 lubricant Substances 0.000 claims description 10
239000003085 diluting agent Substances 0.000 claims description 9
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
239000007884 disintegrant Substances 0.000 claims description 6
239000011975 tartaric acid Substances 0.000 claims description 6
235000002906 tartaric acid Nutrition 0.000 claims description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
239000003381 stabilizer Substances 0.000 claims description 4
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
239000011976 maleic acid Substances 0.000 claims description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 3
239000002562 thickening agent Substances 0.000 claims 1
239000000203 mixture Substances 0.000 description 15
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
238000002360 preparation method Methods 0.000 description 9
239000013078 crystal Substances 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000005303 weighing Methods 0.000 description 8
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 6
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 6
230000000052 comparative effect Effects 0.000 description 6
239000003937 drug carrier Substances 0.000 description 6
239000001863 hydroxypropyl cellulose Substances 0.000 description 6
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 6
239000008101 lactose Substances 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
239000000546 pharmaceutical excipient Substances 0.000 description 6
229940124531 pharmaceutical excipient Drugs 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000002775 capsule Substances 0.000 description 5
238000007906 compression Methods 0.000 description 5
230000006835 compression Effects 0.000 description 5
239000012530 fluid Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 5
229920002472 Starch Polymers 0.000 description 4
239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
229920002678 cellulose Polymers 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
235000010980 cellulose Nutrition 0.000 description 3
238000010494 dissociation reaction Methods 0.000 description 3
230000005593 dissociations Effects 0.000 description 3
238000009826 distribution Methods 0.000 description 3
238000009477 fluid bed granulation Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
238000012360 testing method Methods 0.000 description 3
102000016912 Aldehyde Reductase Human genes 0.000 description 2
108010053754 Aldehyde reductase Proteins 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
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 2
VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
229950008138 carmellose Drugs 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
230000001186 cumulative effect Effects 0.000 description 2
208000002925 dental caries Diseases 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000012085 test solution Substances 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
239000004386 Erythritol Substances 0.000 description 1
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 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
229920000881 Modified starch Polymers 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
239000004373 Pullulan Substances 0.000 description 1
229920001218 Pullulan Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 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
229930006000 Sucrose Natural products 0.000 description 1
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
239000002253 acid 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
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013736 caramel Nutrition 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
238000010586 diagram Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000007908 dry granulation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
229940009714 erythritol Drugs 0.000 description 1
235000019414 erythritol Nutrition 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
238000009478 high shear granulation Methods 0.000 description 1
239000001341 hydroxy propyl starch Substances 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
235000013828 hydroxypropyl starch Nutrition 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
229960003511 macrogol Drugs 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002304 perfume Substances 0.000 description 1
230000035699 permeability Effects 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229940068965 polysorbates Drugs 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
235000019423 pullulan Nutrition 0.000 description 1
238000004080 punching Methods 0.000 description 1
238000004445 quantitative analysis Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
229960002920 sorbitol Drugs 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000001959 sucrose esters of fatty acids Substances 0.000 description 1
235000010965 sucrose esters of fatty acids Nutrition 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
239000000811 xylitol Substances 0.000 description 1
235000010447 xylitol Nutrition 0.000 description 1
229960002675 xylitol Drugs 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/499—Spiro-condensed pyrazines or piperazines
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- A61K47/02—Inorganic compounds
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Diabetes (AREA)
Molecular Biology (AREA)
Biophysics (AREA)
Endocrinology (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Hematology (AREA)
Obesity (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Cosmetics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Saccharide Compounds (AREA)

NO20002049A 1997-10-20 2000-04-18 Hurtigopplosende farmasoytisk preparat som omfatter mikronisert (R)-2-(4-brom-2-fluorbenzyl)-1,2,3,4-tetrahydropyrrol[1,2-a]pyrazin-4-spiro-3'-pyrrolidin-1,2',3,5'-tetron NO319049B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP30663597		1997-10-20
PCT/JP1998/004658 WO1999020277A1 (fr)	1997-10-20	1998-10-15	Composition medicamenteuse a dissolution rapide

Publications (3)

Publication Number	Publication Date
NO20002049D0 NO20002049D0 (no)	2000-04-18
NO20002049L NO20002049L (no)	2000-06-19
NO319049B1 true NO319049B1 (no)	2005-06-06

Family

ID=17959478

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20002049A NO319049B1 (no)	1997-10-20	2000-04-18	Hurtigopplosende farmasoytisk preparat som omfatter mikronisert (R)-2-(4-brom-2-fluorbenzyl)-1,2,3,4-tetrahydropyrrol[1,2-a]pyrazin-4-spiro-3'-pyrrolidin-1,2',3,5'-tetron

Country Status (22)

Country	Link
US (2)	US7141249B2 (pt)
EP (1)	EP1033132B1 (pt)
KR (1)	KR100571614B1 (pt)
CN (1)	CN1156277C (pt)
AT (1)	ATE296101T1 (pt)
AU (1)	AU740299B2 (pt)
BR (1)	BR9814090A (pt)
CA (1)	CA2306883C (pt)
CZ (1)	CZ299018B6 (pt)
DE (1)	DE69830333T2 (pt)
ES (1)	ES2242298T3 (pt)
HK (1)	HK1030359A1 (pt)
HU (1)	HUP0004132A3 (pt)
ID (1)	ID23915A (pt)
NO (1)	NO319049B1 (pt)
NZ (1)	NZ503796A (pt)
PL (1)	PL191533B1 (pt)
PT (1)	PT1033132E (pt)
RU (1)	RU2203665C2 (pt)
TR (1)	TR200001056T2 (pt)
TW (1)	TW592728B (pt)
WO (1)	WO1999020277A1 (pt)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2306883C (en) *	1997-10-20	2007-11-27	Dainippon Pharmaceutical Co., Ltd.	Fast-dissolving pharmaceutical composition comprising as-3201
CN102048734B (zh)	2005-05-26	2013-11-20	大日本住友制药株式会社	药物组合物
CA2733778A1 (en) *	2008-08-14	2010-02-18	Hiroshi Uchida	Stabilized pharmaceutical composition
CN105769809A (zh) *	2014-12-23	2016-07-20	上海星泰医药科技有限公司	提高生物利用度的雷尼司他及其制备方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK607188A (da) *	1987-11-02	1989-06-22	Merck & Co Inc	Tablet indeholdende en phthalazineddikesyreforbindelse
TW202450B (pt)	1991-06-26	1993-03-21	Dainippon Pharmaceutical Co
JPH0518672A (ja) *	1991-07-09	1993-01-26	Daido Steel Co Ltd	熱処理炉の冷却域における炉体構造
DE4141351A1 (de) *	1991-12-14	1993-06-17	Basf Ag	Stabile pulverfoermige vitamin- und/oder carotinoid-praeparate und verfahren zu deren herstellung
DE4400464A1 (de) *	1994-01-11	1995-07-13	Bayer Ag	Endoparasitizide Mittel
DE4440337A1 (de) *	1994-11-11	1996-05-15	Dds Drug Delivery Services Ges	Pharmazeutische Nanosuspensionen zur Arzneistoffapplikation als Systeme mit erhöhter Sättigungslöslichkeit und Lösungsgeschwindigkeit
TWI238064B (en) *	1995-06-20	2005-08-21	Takeda Chemical Industries Ltd	A pharmaceutical composition for prophylaxis and treatment of diabetes
US6458811B1 (en) *	1996-03-26	2002-10-01	Eli Lilly And Company	Benzothiophenes formulations containing same and methods
CA2306883C (en) *	1997-10-20	2007-11-27	Dainippon Pharmaceutical Co., Ltd.	Fast-dissolving pharmaceutical composition comprising as-3201
PT1038525E (pt) *	1997-10-20	2004-11-30	Dainippon Pharmaceutical Co	Composicoes farmaceuticas estabilizadas

1998
- 1998-10-15 CA CA002306883A patent/CA2306883C/en not_active Expired - Fee Related
- 1998-10-15 CZ CZ20001418A patent/CZ299018B6/cs not_active IP Right Cessation
- 1998-10-15 US US09/529,715 patent/US7141249B2/en not_active Expired - Fee Related
- 1998-10-15 ID IDW20000676A patent/ID23915A/id unknown
- 1998-10-15 AU AU94619/98A patent/AU740299B2/en not_active Ceased
- 1998-10-15 TR TR2000/01056T patent/TR200001056T2/xx unknown
- 1998-10-15 KR KR1020007004191A patent/KR100571614B1/ko not_active IP Right Cessation
- 1998-10-15 ES ES98947883T patent/ES2242298T3/es not_active Expired - Lifetime
- 1998-10-15 AT AT98947883T patent/ATE296101T1/de active
- 1998-10-15 WO PCT/JP1998/004658 patent/WO1999020277A1/ja active IP Right Grant
- 1998-10-15 CN CNB98812372XA patent/CN1156277C/zh not_active Expired - Fee Related
- 1998-10-15 PT PT98947883T patent/PT1033132E/pt unknown
- 1998-10-15 HU HU0004132A patent/HUP0004132A3/hu unknown
- 1998-10-15 DE DE69830333T patent/DE69830333T2/de not_active Expired - Lifetime
- 1998-10-15 BR BR9814090-6A patent/BR9814090A/pt not_active Application Discontinuation
- 1998-10-15 NZ NZ503796A patent/NZ503796A/en not_active IP Right Cessation
- 1998-10-15 EP EP98947883A patent/EP1033132B1/en not_active Expired - Lifetime
- 1998-10-15 RU RU2000112538/14A patent/RU2203665C2/ru not_active IP Right Cessation
- 1998-10-15 PL PL340045A patent/PL191533B1/pl not_active IP Right Cessation
- 1998-10-19 TW TW087117258A patent/TW592728B/zh not_active IP Right Cessation
2000
- 2000-04-18 NO NO20002049A patent/NO319049B1/no not_active IP Right Cessation
2001
- 2001-01-29 HK HK01100617A patent/HK1030359A1/xx not_active IP Right Cessation
2006
- 2006-08-03 US US11/498,147 patent/US20060269599A1/en not_active Abandoned

Also Published As

Publication number	Publication date
AU740299B2 (en)	2001-11-01
EP1033132B1 (en)	2005-05-25
DE69830333T2 (de)	2006-01-26
NO20002049D0 (no)	2000-04-18
ATE296101T1 (de)	2005-06-15
HUP0004132A3 (en)	2006-06-28
CA2306883C (en)	2007-11-27
ID23915A (id)	2000-05-25
PT1033132E (pt)	2005-09-30
DE69830333D1 (de)	2005-06-30
US20060269599A1 (en)	2006-11-30
CN1156277C (zh)	2004-07-07
CN1282246A (zh)	2001-01-31
WO1999020277A1 (fr)	1999-04-29
NO20002049L (no)	2000-06-19
RU2203665C2 (ru)	2003-05-10
EP1033132A8 (en)	2001-04-04
ES2242298T3 (es)	2005-11-01
PL340045A1 (en)	2001-01-15
US7141249B2 (en)	2006-11-28
BR9814090A (pt)	2000-10-03
KR100571614B1 (ko)	2006-04-17
TW592728B (en)	2004-06-21
HK1030359A1 (en)	2001-05-04
NZ503796A (en)	2001-11-30
CZ299018B6 (cs)	2008-04-02
KR20010015781A (ko)	2001-02-26
CA2306883A1 (en)	1999-04-29
CZ20001418A3 (cs)	2000-10-11
EP1033132A1 (en)	2000-09-06
AU9461998A (en)	1999-05-10
PL191533B1 (pl)	2006-06-30
US20020197308A1 (en)	2002-12-26
TR200001056T2 (tr)	2000-09-21
HUP0004132A2 (hu)	2001-08-28

Legal Events

Date	Code	Title	Description
2015-05-26	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US20030099698A1 (en)	2003-05-29	Storage stable thyroxine active drug formulations and methods for their production
US20090292016A1 (en)	2009-11-26	Stable Pharmaceutical Compositions Containing Pravastatin
NO319049B1 (no)	2005-06-06	Hurtigopplosende farmasoytisk preparat som omfatter mikronisert (R)-2-(4-brom-2-fluorbenzyl)-1,2,3,4-tetrahydropyrrol[1,2-a]pyrazin-4-spiro-3'-pyrrolidin-1,2',3,5'-tetron
US20030096014A1 (en)	2003-05-22	Solid pharmaceutical compositions for oral administration comprising itraconazole
EP0636023B1 (en)	1999-08-11	Aminoguanidine spray drying process
EP1864677B1 (en)	2008-01-02	Stable formulation comprising a moisture sensitive drug and manufacturing procedure thereof
WO2010077669A2 (en)	2010-07-08	Palonosetron formulation
US20070281000A1 (en)	2007-12-06	Stable formulation comprising moisture sensitive drug/s and manufacturing procedure thereof
WO2007142628A1 (en)	2007-12-13	Stable formulation comprising moisture sensitive drug/s and manufacturing procedure thereof
US6245785B1 (en)	2001-06-12	Dissolution of triprolidine hydrochloride
MXPA00003747A (en)	2001-03-05	Rapidly soluble drug composition
US20040151768A1 (en)	2004-08-05	Pharmaceutical compositions containing an effervescent acid-base couple
JP2007246539A (ja)	2007-09-27	速溶性医薬組成物
AU2002314915A1 (en)	2003-01-08	Stable pharmaceutical compositions containing pravastatin
CA2659814A1 (en)	2008-01-17	Stable formulation comprising a combination of a moisture sensitive drug and a second drug and manufacturing procedure thereof