CA2537480A1 - Nouvelle forme galenique orale pour ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyle)-phenylamino]-methyle-1-methyle-1h-benzimidazol-5-carbonyle)-pyridine-2-yle-amino]propionique et ses sels - Google Patents

Nouvelle forme galenique orale pour ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyle)-phenylamino]-methyle-1-methyle-1h-benzimidazol-5-carbonyle)-pyridine-2-yle-amino]propionique et ses sels Download PDF

Info

Publication number: CA2537480A1
Authority: CA; Canada
Prior art keywords: methyl; pharmaceutical composition; hexyloxycarbonylamino; imino; pyridin
Prior art date: 2003-09-03
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.): Abandoned

Application number

CA002537480A

Other languages

English (en)

Inventor

Guido B. E. Radtke

Ulrich Busch

Achim Sauer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim International GmbH

Original Assignee

Individual

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.)

2003-09-03

Filing date

2004-08-28

Publication date

2005-03-17

2004-08-28 Application filed by Individual filed Critical Individual

2005-03-17 Publication of CA2537480A1 publication Critical patent/CA2537480A1/fr

Status Abandoned legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 title claims abstract description 12
-1 2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1h-benzimidazol-5-carbonyl Chemical group 0.000 title abstract description 5
239000002552 dosage form Substances 0.000 title abstract 2
239000013543 active substance Substances 0.000 claims abstract description 31
150000001875 compounds Chemical class 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 27
239000008194 pharmaceutical composition Substances 0.000 claims description 17
239000003381 stabilizer Substances 0.000 claims description 14
239000002775 capsule Substances 0.000 claims description 11
239000004615 ingredient Substances 0.000 claims description 10
239000007902 hard capsule Substances 0.000 claims description 9
238000002844 melting Methods 0.000 claims description 8
SEGHHPAKTYKSLB-UHFFFAOYSA-N ethyl 3-[[2-[[4-[(hexoxycarbonylhydrazinylidene)methyl]anilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate Chemical compound C1=CC(C=NNC(=O)OCCCCCC)=CC=C1NCC1=NC2=CC(C(=O)N(CCC(=O)OCC)C=3N=CC=CC=3)=CC=C2N1C SEGHHPAKTYKSLB-UHFFFAOYSA-N 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
239000012141 concentrate Substances 0.000 claims description 5
239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 5
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 5
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
239000004530 micro-emulsion Substances 0.000 claims description 5
239000004094 surface-active agent Substances 0.000 claims description 5
MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 claims description 4
229960003511 macrogol Drugs 0.000 claims description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 3
239000001828 Gelatine Substances 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 3
XETBXHPXHHOLOE-UHFFFAOYSA-N dabigatran etexilate methanesulfonate Chemical compound CS(O)(=O)=O.C1=CC(C(\N)=N/C(=O)OCCCCCC)=CC=C1NCC1=NC2=CC(C(=O)N(CCC(=O)OCC)C=3N=CC=CC=3)=CC=C2N1C XETBXHPXHHOLOE-UHFFFAOYSA-N 0.000 claims description 3
229920000159 gelatin Polymers 0.000 claims description 3
235000019322 gelatine Nutrition 0.000 claims description 3
ARIWANIATODDMH-UHFFFAOYSA-N Lauric acid monoglyceride Natural products CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 claims 4
239000007970 homogeneous dispersion Substances 0.000 claims 3
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 claims 1
238000010348 incorporation Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
238000012856 packing Methods 0.000 claims 1
238000009472 formulation Methods 0.000 description 20
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 7
239000003929 acidic solution Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 description 5
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 5
229940070765 laurate Drugs 0.000 description 5
229960005019 pantoprazole Drugs 0.000 description 5
238000011282 treatment Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 4
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
230000008018 melting Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
210000002784 stomach Anatomy 0.000 description 4
229930003799 tocopherol Natural products 0.000 description 4
239000011732 tocopherol Substances 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
206010025476 Malabsorption Diseases 0.000 description 3
208000004155 Malabsorption Syndromes Diseases 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
230000036470 plasma concentration Effects 0.000 description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
229920000053 polysorbate 80 Polymers 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000002203 pretreatment Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
229920000858 Cyclodextrin Polymers 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
108090000190 Thrombin Proteins 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
125000005456 glyceride group Chemical group 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000007901 soft capsule Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229960004072 thrombin Drugs 0.000 description 2
235000010384 tocopherol Nutrition 0.000 description 2
229960001295 tocopherol Drugs 0.000 description 2
235000019149 tocopherols Nutrition 0.000 description 2
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 2
WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
FUWVMBCPMRAWPG-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-hydroxyoctadecanoate Chemical compound CCCCCCCCCCCCCCCCC(O)C(=O)OCC(O)CO FUWVMBCPMRAWPG-UHFFFAOYSA-N 0.000 description 1
WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.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 WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
241000195493 Cryptophyta 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
206010051055 Deep vein thrombosis Diseases 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
239000004368 Modified starch Substances 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
206010047249 Venous thrombosis Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000007605 air drying Methods 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229940124301 concurrent medication Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229960000913 crospovidone Drugs 0.000 description 1
KSGXQBZTULBEEQ-UHFFFAOYSA-N dabigatran etexilate Chemical compound C1=CC(C(N)=NC(=O)OCCCCCC)=CC=C1NCC1=NC2=CC(C(=O)N(CCC(=O)OCC)C=3N=CC=CC=3)=CC=C2N1C KSGXQBZTULBEEQ-UHFFFAOYSA-N 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000003925 fat Substances 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
229930003935 flavonoid Natural products 0.000 description 1
150000002215 flavonoids Chemical class 0.000 description 1
235000017173 flavonoids Nutrition 0.000 description 1
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical class OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
229940116364 hard fat Drugs 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229960001021 lactose monohydrate Drugs 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
HCZKYJDFEPMADG-TXEJJXNPSA-N masoprocol Chemical compound C([C@H](C)[C@H](C)CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-TXEJJXNPSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
229940068965 polysorbates Drugs 0.000 description 1
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229940075554 sorbate Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000020238 sunflower seed Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
150000005691 triesters Chemical class 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
239000010497 wheat germ oil Substances 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- 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
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds

Landscapes

Health & Medical Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Hematology (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002537480A 2003-09-03 2004-08-28 Nouvelle forme galenique orale pour ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyle)-phenylamino]-methyle-1-methyle-1h-benzimidazol-5-carbonyle)-pyridine-2-yle-amino]propionique et ses sels Abandoned CA2537480A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE10341043A DE10341043A1 (de)	2003-09-03	2003-09-03	Neue oral zu applizierende Darreichungsform für 3-[(2-{[4-Hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionsäure-ethylester und dessen Salze
DE10341043.0		2003-09-03
PCT/EP2004/009619 WO2005023249A1 (fr)	2003-09-03	2004-08-28	Nouvelle forme galenique orale pour ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyle)-phenylamino]-methyle-1-methyle-1h-benzimidazol-5-carbonyle)-pyridine-2-yle-amino]propionique et ses sels

Publications (1)

Publication Number	Publication Date
CA2537480A1 true CA2537480A1 (fr)	2005-03-17

Family

ID=34223394

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002537480A Abandoned CA2537480A1 (fr)	2003-09-03	2004-08-28	Nouvelle forme galenique orale pour ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyle)-phenylamino]-methyle-1-methyle-1h-benzimidazol-5-carbonyle)-pyridine-2-yle-amino]propionique et ses sels

Country Status (5)

Country	Link
EP (1)	EP1663209A1 (fr)
JP (1)	JP2007504190A (fr)
CA (1)	CA2537480A1 (fr)
DE (1)	DE10341043A1 (fr)
WO (1)	WO2005023249A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MX2009000602A (es) *	2006-07-17	2009-01-28	Boehringer Ingelheim Int	Nuevas indicaciones para los inhibidores directos de la trombina en el campo cardiovascular.
JP2013521318A (ja)	2010-03-08	2013-06-10	ラティオファルムゲー・エム・ベー・ハー	ダビガトランエテキシラートを含有する医薬組成物
PL2588090T3 (pl)	2010-07-01	2017-12-29	Krka, Tovarna Zdravil, D.D., Novo Mesto	Doustne farmaceutyczne postacie dawkowania zawierające eteksylan dabigatranu i jego farmaceutycznie dopuszczalne sole
PL2603503T3 (pl)	2010-09-27	2015-12-31	Ratiopharm Gmbh	Sól bismesylanowa eteksylanu dabigatranu, postacie stałe i sposób ich otrzymywania
PL2550966T3 (pl)	2011-07-25	2017-03-31	Dritte Patentportfolio Beteiligungsgesellschaft Mbh & Co. Kg	Estry kwasu amidooksymokarboksylowego dabigatranu jako proleki i ich zastosowanie jako lek

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PE121699A1 (es) *	1997-02-18	1999-12-08	Boehringer Ingelheim Pharma	Heterociclos biciclicos disustituidos como inhibidores de la trombina
US6200968B1 (en) *	1998-08-06	2001-03-13	Cephalon, Inc.	Particle-forming compositions containing fused pyrrolocarbazoles
GB0029843D0 (en) *	2000-12-07	2001-01-24	Univ Belfast	Drug delivery system
DE10133786A1 (de) *	2001-07-16	2003-02-06	Boehringer Ingelheim Pharma	Verwendung von Thrombin-Inhibitoren zur Behandlung von Arthritis
CA2476054C (fr) *	2002-03-07	2011-11-08	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Forme pharmaceutique pour administration orale a base d'ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1methyl-1h-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionique ou dw ses sels pharmaceutiquement acceptables

2003
- 2003-09-03 DE DE10341043A patent/DE10341043A1/de not_active Withdrawn
2004
- 2004-08-28 JP JP2006525085A patent/JP2007504190A/ja active Pending
- 2004-08-28 EP EP04764593A patent/EP1663209A1/fr not_active Withdrawn
- 2004-08-28 WO PCT/EP2004/009619 patent/WO2005023249A1/fr not_active Ceased
- 2004-08-28 CA CA002537480A patent/CA2537480A1/fr not_active Abandoned

Also Published As

Publication number	Publication date
EP1663209A1 (fr)	2006-06-07
DE10341043A1 (de)	2005-03-31
JP2007504190A (ja)	2007-03-01
WO2005023249A1 (fr)	2005-03-17

Legal Events

Date	Code	Title	Description
2008-08-28	FZDE	Dead

Publication	Publication Date	Title
US5876749A (en)	1999-03-02	Pharmaceutical composition
CA2535810C (fr)	2013-06-25	Comprime contenant l'ethylester de l'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1h-benzimidazol-5-carbonyl)-pyridin-2-yl)amino]-propioniqueou ses sels
US10543196B2 (en)	2020-01-28	Oral dosage forms of bendamustine
JP2005518423A (ja)	2005-06-23	Ｃ型肝炎ウイルスプロテアーゼインヒビター用の医薬組成物
AU2006295440A1 (en)	2007-04-05	Capsule formulation of pirfenidone and pharmaceutically acceptable excipients
CZ299728B6 (cs)	2008-11-05	Farmaceutická kompozice
JPWO2008066102A1 (ja)	2010-03-11	徐放性製剤
EP4054537B1 (fr)	2023-06-07	Formulation orale de x842
US20050107438A1 (en)	2005-05-19	Pharmaceutical composition comprising 3-[(2-{[4-(Hexyloxycarbonylaminoiminomethyl) phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester or a salt therefore
JP2015013857A (ja)	2015-01-22	被覆製剤
KR101725462B1 (ko)	2017-04-11	칼슘 길항약／안지오텐신 ｉｉ 수용체 길항약 함유 의약 제제
CA2800279A1 (fr)	2011-12-08	Formes galeniques orales de bendamustine
EP2310385B1 (fr)	2017-06-07	Composition pharmaceutique solide
RS57027B1 (sr)	2018-05-31	Farmaceutski dozni oblik koji sadrži 6’-fluoro-(n-metil- ili n,n-dimetil-)-4-fenil-4’,9’-dihidro-3’h-spiro[ciloheksan-1,1’-pirano[3,4,b]indol]-4-amin
CA2537480A1 (fr)	2005-03-17	Nouvelle forme galenique orale pour ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyle)-phenylamino]-methyle-1-methyle-1h-benzimidazol-5-carbonyle)-pyridine-2-yle-amino]propionique et ses sels
US20060099230A1 (en)	2006-05-11	Novel formulations of eprosartan with enhanced bioavailability
KR20240102908A (ko)	2024-07-03	아픽사반을 포함하는 서방성 정제
WO2014053974A1 (fr)	2014-04-10	Compositions pharmaceutiques de sirolimus
KR101052947B1 (ko)	2011-07-29	아젤라스틴 액상 제제
JPH02129123A (ja)	1990-05-17	抗血液凝固剤
AU2013201986A1 (en)	2013-04-18	Capsule Formulation Of Pirfenidone And Pharmaceutically Acceptable Excipients
KR20210079003A (ko)	2021-06-29	안지오텐신 수용체 길항제를 포함하는 약제학적 조성물 및 이의 제조방법