KR20120027142A - 무정형 알파-(ｎ-술폰아미도)아세트아미드 화합물의 생체이용가능한 조성물 - Google Patents
무정형 알파-(ｎ-술폰아미도)아세트아미드 화합물의 생체이용가능한 조성물 Download PDFInfo
- Publication number
- KR20120027142A KR20120027142A KR1020117024035A KR20117024035A KR20120027142A KR 20120027142 A KR20120027142 A KR 20120027142A KR 1020117024035 A KR1020117024035 A KR 1020117024035A KR 20117024035 A KR20117024035 A KR 20117024035A KR 20120027142 A KR20120027142 A KR 20120027142A
- Authority
- KR
- South Korea
- Prior art keywords
- composition
- phenyl
- trifluoropentanamide
- sulfonyl
- fluoro
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- -1 acetamide compound Chemical class 0.000 title description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 26
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims abstract description 19
- 239000007962 solid dispersion Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 19
- FYUWIEKAVLOHSE-UHFFFAOYSA-N ethenyl acetate;1-ethenylpyrrolidin-2-one Chemical compound CC(=O)OC=C.C=CN1CCCC1=O FYUWIEKAVLOHSE-UHFFFAOYSA-N 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 10
- XEAOPVUAMONVLA-QGZVFWFLSA-N Avagacestat Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N([C@H](CCC(F)(F)F)C(=O)N)CC(C(=C1)F)=CC=C1C=1N=CON=1 XEAOPVUAMONVLA-QGZVFWFLSA-N 0.000 claims description 7
- 238000009474 hot melt extrusion Methods 0.000 claims description 7
- 238000001694 spray drying Methods 0.000 claims description 7
- 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 26
- 208000024827 Alzheimer disease Diseases 0.000 description 22
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 description 16
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 201000010099 disease Diseases 0.000 description 9
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 description 8
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 7
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 7
- 201000002832 Lewy body dementia Diseases 0.000 description 7
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 201000008319 inclusion body myositis Diseases 0.000 description 6
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 description 5
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 description 5
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 description 5
- 102000014736 Notch Human genes 0.000 description 5
- 108010070047 Notch Receptors Proteins 0.000 description 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 5
- 208000010877 cognitive disease Diseases 0.000 description 5
- 239000003540 gamma secretase inhibitor Substances 0.000 description 5
- 206010012289 Dementia Diseases 0.000 description 4
- 201000010374 Down Syndrome Diseases 0.000 description 4
- 102100022033 Presenilin-1 Human genes 0.000 description 4
- 108010036933 Presenilin-1 Proteins 0.000 description 4
- 108010036908 Presenilin-2 Proteins 0.000 description 4
- 108010064539 amyloid beta-protein (1-42) Proteins 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 208000002780 macular degeneration Diseases 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 208000027061 mild cognitive impairment Diseases 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 102100022036 Presenilin-2 Human genes 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 208000030886 Traumatic Brain injury Diseases 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 206010064930 age-related macular degeneration Diseases 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000035772 mutation Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000009529 traumatic brain injury Effects 0.000 description 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 2
- 241000220479 Acacia Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000037259 Amyloid Plaque Diseases 0.000 description 2
- 102100021257 Beta-secretase 1 Human genes 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229940125373 Gamma-Secretase Inhibitor Drugs 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 206010019196 Head injury Diseases 0.000 description 2
- 101000894895 Homo sapiens Beta-secretase 1 Proteins 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 2
- 235000012216 bentonite Nutrition 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 208000017004 dementia pugilistica Diseases 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 210000004558 lewy body Anatomy 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 210000003583 retinal pigment epithelium Anatomy 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 230000011664 signaling Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WABLSWMRHNIUFN-UHFFFAOYSA-N 1-(1,1-dioxothiadiaziridin-2-yl)ethanone Chemical class C(C)(=O)N1S(=O)(=O)N1 WABLSWMRHNIUFN-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- FYLZPFSWVMMCQC-UHFFFAOYSA-N 5,5,5-trifluoropentanamide Chemical compound NC(=O)CCCC(F)(F)F FYLZPFSWVMMCQC-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 206010002329 Aneurysm Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010007759 Cataract nuclear Diseases 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 206010012239 Delusion Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000237858 Gastropoda Species 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
- 206010019075 Hallucination, visual Diseases 0.000 description 1
- 208000004547 Hallucinations Diseases 0.000 description 1
- 208000016988 Hemorrhagic Stroke Diseases 0.000 description 1
- 208000009829 Lewy Body Disease Diseases 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- 102000008300 Mutant Proteins Human genes 0.000 description 1
- 108010021466 Mutant Proteins Proteins 0.000 description 1
- 102000006386 Myelin Proteins Human genes 0.000 description 1
- 108010083674 Myelin Proteins Proteins 0.000 description 1
- 238000011887 Necropsy Methods 0.000 description 1
- 206010029240 Neuritis Diseases 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- 101000579647 Penaeus vannamei Penaeidin-2a Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004349 Polyvinylpyrrolidone-vinyl acetate copolymer Substances 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 102100040347 TAR DNA-binding protein 43 Human genes 0.000 description 1
- 101710150875 TAR DNA-binding protein 43 Proteins 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 108091005906 Type I transmembrane proteins Proteins 0.000 description 1
- 102000044159 Ubiquitin Human genes 0.000 description 1
- 108090000848 Ubiquitin Proteins 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- ZUAAPNNKRHMPKG-UHFFFAOYSA-N acetic acid;butanedioic acid;methanol;propane-1,2-diol Chemical compound OC.CC(O)=O.CC(O)CO.OC(=O)CCC(O)=O ZUAAPNNKRHMPKG-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 108010064397 amyloid beta-protein (1-40) Proteins 0.000 description 1
- 230000003941 amyloidogenesis Effects 0.000 description 1
- 206010002022 amyloidosis Diseases 0.000 description 1
- 101150089041 aph-1 gene Proteins 0.000 description 1
- 201000007201 aphasia Diseases 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000008901 benefit Effects 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 201000011529 cardiovascular cancer Diseases 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 231100000868 delusion Toxicity 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
- 208000023060 memory loss Diseases 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
- 238000003801 milling Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007659 motor function Effects 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 210000005012 myelin Anatomy 0.000 description 1
- 210000004126 nerve fiber Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 102000046701 nicastrin Human genes 0.000 description 1
- 108700022821 nicastrin Proteins 0.000 description 1
- 208000029552 nuclear cataract Diseases 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000005959 oncogenic signaling Effects 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000019448 polyvinylpyrrolidone-vinyl acetate copolymer Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000006337 proteolytic cleavage Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 238000009491 slugging Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 108091005703 transmembrane proteins Proteins 0.000 description 1
- 102000035160 transmembrane proteins Human genes 0.000 description 1
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
- 239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229930195724 β-lactose Natural products 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
- A61K31/41—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
- A61K31/4245—Oxadiazoles
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16906609P | 2009-04-14 | 2009-04-14 | |
| US61/169,066 | 2009-04-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20120027142A true KR20120027142A (ko) | 2012-03-21 |
Family
ID=42664672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117024035A Withdrawn KR20120027142A (ko) | 2009-04-14 | 2010-04-12 | 무정형 알파-(ｎ-술폰아미도)아세트아미드 화합물의 생체이용가능한 조성물 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20100261768A1 (enExample) |
| EP (1) | EP2419086B1 (enExample) |
| JP (1) | JP2012524090A (enExample) |
| KR (1) | KR20120027142A (enExample) |
| CN (1) | CN102387788B (enExample) |
| AR (1) | AR076306A1 (enExample) |
| AU (1) | AU2010236701A1 (enExample) |
| BR (1) | BRPI1012523A2 (enExample) |
| CA (1) | CA2758709A1 (enExample) |
| DK (1) | DK2419086T3 (enExample) |
| EA (1) | EA201171207A1 (enExample) |
| ES (1) | ES2426403T3 (enExample) |
| HR (1) | HRP20130807T1 (enExample) |
| MX (1) | MX2011010513A (enExample) |
| NZ (1) | NZ595411A (enExample) |
| PL (1) | PL2419086T3 (enExample) |
| PT (1) | PT2419086E (enExample) |
| SI (1) | SI2419086T1 (enExample) |
| SM (1) | SMT201300106B (enExample) |
| TW (1) | TW201043269A (enExample) |
| WO (1) | WO2010120662A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1289469C (zh) | 2001-12-20 | 2006-12-13 | 布里斯托尔-迈尔斯斯奎布公司 | α－(N－磺酰氨基)乙酰胺衍生物作为β－淀粉样蛋白抑制剂 |
| US8044077B2 (en) | 2009-03-19 | 2011-10-25 | Bristol-Myers Squibb Company | Alpha-(N-sulfonamido)acetamide compounds incorporating deuterium as inhibitors of beta amyloid peptide production |
| US7977362B2 (en) | 2009-03-20 | 2011-07-12 | Bristol-Myers Squibb Company | Alpha-(N-benzenesulfonamido)cycloalkyl derivatives |
| US8252821B2 (en) | 2009-04-14 | 2012-08-28 | Bristol-Myers Squibb Company | Bioavailable capsule compositions of amorphous alpha-(N-sulfonamido)acetamide compound |
| AR087277A1 (es) * | 2011-07-21 | 2014-03-12 | Bristol Myers Squibb Co | Composiciones biodisponibles de compuestos amorfos de piperidinilo, composicion farmaceutica, metodos |
| US20150045353A1 (en) * | 2013-08-09 | 2015-02-12 | Neurogenetic Pharmaceuticals, Inc. | Formulations containing gamma secretase modulators, methods for preparation and delivery thereof |
| TWI765410B (zh) | 2014-08-08 | 2022-05-21 | 日商中外製藥股份有限公司 | ４環性化合物的非晶質體的用途 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3999007A (en) * | 1975-10-09 | 1976-12-21 | Carl Joseph Crane | Aircraft visual approach/landing reproducer device and system |
| US5136301A (en) * | 1989-08-30 | 1992-08-04 | Rockwell International Corporation | Primary flight display system having a vertical linear altimeter |
| US5274094A (en) * | 1990-08-15 | 1993-12-28 | British Bio-Technology Limited | Production of heterobicyclic containing benzene sulfonamides |
| GB9202791D0 (en) * | 1992-02-11 | 1992-03-25 | British Bio Technology | Compounds |
| DE69606804T2 (de) * | 1995-06-20 | 2000-06-15 | Honeywell, Inc. | Integriertes System zur Grundkollisionsvermeidung |
| US5977141A (en) * | 1995-11-17 | 1999-11-02 | Warner-Lambert Company | Sulfonamide inhibitors of matrix metalloproteinases |
| US6233522B1 (en) * | 1998-07-06 | 2001-05-15 | Alliedsignal Inc. | Aircraft position validation using radar and digital terrain elevation database |
| US6313123B1 (en) * | 1999-01-27 | 2001-11-06 | American Cyanamid Company | Acetylenic sulfonamide thiol tace inhibitors |
| US6570531B1 (en) * | 2000-04-27 | 2003-05-27 | Rockwell Collins, Inc. | Satellite navigation receiver designed for compatibility with aircraft automatic landing systems |
| US6483454B1 (en) * | 2000-11-28 | 2002-11-19 | Bae Systems Aerospace Inc. | Close formation aircraft collision avoidance |
| CN1289469C (zh) * | 2001-12-20 | 2006-12-13 | 布里斯托尔-迈尔斯斯奎布公司 | α－(N－磺酰氨基)乙酰胺衍生物作为β－淀粉样蛋白抑制剂 |
| CN101274926A (zh) * | 2003-03-31 | 2008-10-01 | 惠氏公司 | β淀粉样蛋白生成抑制剂含氟和三氟烷基杂环磺酰胺及其衍生物 |
| US20050048112A1 (en) * | 2003-08-28 | 2005-03-03 | Jorg Breitenbach | Solid pharmaceutical dosage form |
| FR2870605B1 (fr) * | 2004-05-18 | 2010-10-08 | Airbus France | Procede et dispositif de guidage automatique d'un aeronef, pour un vol au moins en partie a basse altitude |
| FR2880456B1 (fr) * | 2005-01-03 | 2007-02-23 | Airbus France Sas | Procede et dispositif d'alerte sonore lors de la desactivation d'un pilote automatique d'un aeronef |
| FR2886439B1 (fr) * | 2005-05-24 | 2010-11-05 | Eurocopter France | Procede et dispositif d'aide au pilotage d'un aeronef a basse altitude |
| CN101384250A (zh) * | 2005-11-09 | 2009-03-11 | 诺瓦提斯公司 | 利用临时增塑剂制备药物组合物的方法 |
| FR2897448B1 (fr) * | 2006-02-14 | 2008-03-14 | Airbus France Sas | Procede et systeme d'aide au pilotage d'un aeronef. |
| JP2009528281A (ja) * | 2006-02-17 | 2009-08-06 | ワイス | スルホンアミド置換アルコールおよびその中間体の調製方法 |
| TW200732295A (en) * | 2006-02-17 | 2007-09-01 | Wyeth Corp | Selective N-sulfonylation of 2-amino trifluoroalkyl substituted alcohols |
| WO2007109604A2 (en) * | 2006-03-20 | 2007-09-27 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions |
| US20070218012A1 (en) * | 2006-03-20 | 2007-09-20 | Bittorf Kevin J | Pharmaceutical Compositions |
| FR2911988B1 (fr) * | 2007-01-26 | 2016-03-25 | Airbus France | Procede et dispositif pour determiner une hauteur maximale de stabilisation lors de la phase finale de vol d'un avion |
| US8084477B2 (en) * | 2007-10-31 | 2011-12-27 | Bristol-Myers Squibb Company | Alpha-(N-sulfonamido)acetamide compound as an inhibitor of beta amyloid peptide production |
-
2010
- 2010-04-08 TW TW099110918A patent/TW201043269A/zh unknown
- 2010-04-09 US US12/757,304 patent/US20100261768A1/en not_active Abandoned
- 2010-04-12 CA CA2758709A patent/CA2758709A1/en not_active Abandoned
- 2010-04-12 BR BRPI1012523A patent/BRPI1012523A2/pt not_active Application Discontinuation
- 2010-04-12 SI SI201030355T patent/SI2419086T1/sl unknown
- 2010-04-12 JP JP2012506089A patent/JP2012524090A/ja active Pending
- 2010-04-12 NZ NZ595411A patent/NZ595411A/xx not_active IP Right Cessation
- 2010-04-12 MX MX2011010513A patent/MX2011010513A/es unknown
- 2010-04-12 WO PCT/US2010/030679 patent/WO2010120662A2/en not_active Ceased
- 2010-04-12 ES ES10714413T patent/ES2426403T3/es active Active
- 2010-04-12 CN CN2010800160778A patent/CN102387788B/zh not_active Expired - Fee Related
- 2010-04-12 EA EA201171207A patent/EA201171207A1/ru unknown
- 2010-04-12 KR KR1020117024035A patent/KR20120027142A/ko not_active Withdrawn
- 2010-04-12 HR HRP20130807AT patent/HRP20130807T1/hr unknown
- 2010-04-12 PT PT107144131T patent/PT2419086E/pt unknown
- 2010-04-12 EP EP10714413.1A patent/EP2419086B1/en not_active Not-in-force
- 2010-04-12 DK DK10714413.1T patent/DK2419086T3/da active
- 2010-04-12 AU AU2010236701A patent/AU2010236701A1/en not_active Abandoned
- 2010-04-12 PL PL10714413T patent/PL2419086T3/pl unknown
- 2010-04-14 AR ARP100101258A patent/AR076306A1/es unknown
-
2013
- 2013-09-24 SM SM201300106T patent/SMT201300106B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2011010513A (es) | 2011-11-29 |
| PL2419086T3 (pl) | 2013-11-29 |
| ES2426403T3 (es) | 2013-10-23 |
| WO2010120662A3 (en) | 2011-09-15 |
| EP2419086B1 (en) | 2013-06-26 |
| DK2419086T3 (da) | 2013-09-30 |
| CN102387788B (zh) | 2013-07-10 |
| PT2419086E (pt) | 2013-09-04 |
| TW201043269A (en) | 2010-12-16 |
| AU2010236701A1 (en) | 2011-10-20 |
| US20100261768A1 (en) | 2010-10-14 |
| SMT201300106B (it) | 2013-11-08 |
| SI2419086T1 (sl) | 2013-10-30 |
| BRPI1012523A2 (pt) | 2016-03-29 |
| EP2419086A2 (en) | 2012-02-22 |
| CN102387788A (zh) | 2012-03-21 |
| AR076306A1 (es) | 2011-06-01 |
| NZ595411A (en) | 2013-02-22 |
| HRP20130807T1 (hr) | 2013-09-30 |
| CA2758709A1 (en) | 2010-10-21 |
| EA201171207A1 (ru) | 2012-03-30 |
| JP2012524090A (ja) | 2012-10-11 |
| WO2010120662A2 (en) | 2010-10-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2419090B1 (en) | Bioavailable capsule compositions of amorphous alpha-(n-sulfonamido)acetamide compound | |
| EP2419086B1 (en) | Bioavailable compositions of amorphous alpha-(n-sulfonamido)acetamide compound | |
| EP1443917B1 (en) | Tamsulosin tablets | |
| ES2390661T3 (es) | Forma de presentación para administración por vía oral para éster etílico de ácido 3-[(2-{[4-(hexiloxicarbonilamino-imino-metil)-fenilamino]-metil}-1-metil-1H-bencimidazol-5-carbonil)-piridin-2-il-amino]-propiónico y sus sales. | |
| CN101448498B (zh) | R(+)和s(-)普拉克索的组合物以及使用该组合物的方法 | |
| CN101069685B (zh) | 固体口服剂型药物 | |
| CA2852618C (en) | Pharmaceutical composition | |
| EP2497473A1 (en) | Therapeutically effective amounts of R(+) and S(-) pramipexole for use in the treatment of Parkinson's disease and pharmaceutical compositions thereof | |
| KR101438546B1 (ko) | 프레가발린을 포함하는 서방성 제제 | |
| JP2016539171A (ja) | アセブロフィリン及び疎水性徐放性基剤を含む徐放性薬学組成物 | |
| US20220249479A1 (en) | Modified release formulation of a pyrimidinylamino-pyrazole compound, and methods of treatment | |
| WO2025218797A1 (zh) | 一种胶囊或固体制剂及其应用 | |
| HK1161108A (en) | Compositions of r(+) and s(-) pramipexole and methods for using the same | |
| NZ718063A (en) | Pharmaceutical dosage forms containing sodium-1-[6-(morpholin-4-yl)pyrimidin-4-yl]-4-(1h-1,2,3-triazol-1-yl)-1h-pyrazol-5-olate | |
| NZ718063B2 (en) | Pharmaceutical dosage forms containing sodium-1-[6-(morpholin-4-yl)pyrimidin-4-yl]-4-(1h-1,2,3-triazol-1-yl)-1h-pyrazol-5-olate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20111013 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |