CA2600603A1 - Formulations of ladostigil tartrate - Google Patents
Formulations of ladostigil tartrate Download PDFInfo
- Publication number
- CA2600603A1 CA2600603A1 CA002600603A CA2600603A CA2600603A1 CA 2600603 A1 CA2600603 A1 CA 2600603A1 CA 002600603 A CA002600603 A CA 002600603A CA 2600603 A CA2600603 A CA 2600603A CA 2600603 A1 CA2600603 A1 CA 2600603A1
- Authority
- CA
- Canada
- Prior art keywords
- pharmaceutical composition
- weight
- amount
- propargyl
- aminoindan
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 238000009472 formulation Methods 0.000 title abstract description 46
- PRLVBVAJMQZMJN-OGOSNNLPSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;[(3r)-3-(prop-2-ynylamino)-2,3-dihydro-1h-inden-5-yl] n-ethyl-n-methylcarbamate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.CCN(C)C(=O)OC1=CC=C2CC[C@@H](NCC#C)C2=C1.CCN(C)C(=O)OC1=CC=C2CC[C@@H](NCC#C)C2=C1 PRLVBVAJMQZMJN-OGOSNNLPSA-N 0.000 title abstract description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 78
- 238000000034 method Methods 0.000 claims abstract description 32
- 230000008569 process Effects 0.000 claims abstract description 14
- -1 N-ethyl-carbamoyloxy Chemical group 0.000 claims description 43
- 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 28
- 229940095064 tartrate Drugs 0.000 claims description 26
- 235000021355 Stearic acid Nutrition 0.000 claims description 24
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 24
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 24
- 230000036470 plasma concentration Effects 0.000 claims description 24
- 239000008117 stearic acid Substances 0.000 claims description 24
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 21
- 210000002381 plasma Anatomy 0.000 claims description 21
- MTVWFVDWRVYDOR-UHFFFAOYSA-N 3,4-Dihydroxyphenylglycol Chemical compound OCC(O)C1=CC=C(O)C(O)=C1 MTVWFVDWRVYDOR-UHFFFAOYSA-N 0.000 claims description 20
- 239000000314 lubricant Substances 0.000 claims description 20
- 239000000945 filler Substances 0.000 claims description 19
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 18
- 229930195725 Mannitol Natural products 0.000 claims description 18
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 18
- 239000000594 mannitol Substances 0.000 claims description 18
- 235000010355 mannitol Nutrition 0.000 claims description 18
- 229920002472 Starch Polymers 0.000 claims description 17
- 239000008107 starch Substances 0.000 claims description 17
- 235000019698 starch Nutrition 0.000 claims description 17
- 239000000454 talc Substances 0.000 claims description 16
- 229910052623 talc Inorganic materials 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 208000024827 Alzheimer disease Diseases 0.000 claims description 13
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical group CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 claims description 13
- 229940045902 sodium stearyl fumarate Drugs 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 239000011230 binding agent Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000007884 disintegrant Substances 0.000 claims description 12
- 206010012289 Dementia Diseases 0.000 claims description 11
- 239000008187 granular material Substances 0.000 claims description 11
- 239000002775 capsule Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000005567 liquid scintillation counting Methods 0.000 claims description 9
- 235000019359 magnesium stearate Nutrition 0.000 claims description 9
- 102000010909 Monoamine Oxidase Human genes 0.000 claims description 8
- 108010062431 Monoamine oxidase Proteins 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 8
- 238000005550 wet granulation Methods 0.000 claims description 8
- 208000012902 Nervous system disease Diseases 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
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- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 4
- 230000001939 inductive effect Effects 0.000 claims description 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000003826 tablet Substances 0.000 claims description 4
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- 208000016620 Tourette disease Diseases 0.000 claims description 3
- 230000006735 deficit Effects 0.000 claims description 3
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- 239000006187 pill Substances 0.000 claims description 3
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- 208000009829 Lewy Body Disease Diseases 0.000 claims description 2
- 201000002832 Lewy body dementia Diseases 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 206010036631 Presenile dementia Diseases 0.000 claims description 2
- 206010039966 Senile dementia Diseases 0.000 claims description 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 2
- 201000004810 Vascular dementia Diseases 0.000 claims description 2
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- 230000000750 progressive effect Effects 0.000 claims description 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 229940032147 starch Drugs 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- LHXOCOHMBFOVJS-OAHLLOKOSA-N Ladostigil Chemical compound CCN(C)C(=O)OC1=CC=C2CC[C@@H](NCC#C)C2=C1 LHXOCOHMBFOVJS-OAHLLOKOSA-N 0.000 description 11
- 229950008812 ladostigil Drugs 0.000 description 11
- 239000012535 impurity Substances 0.000 description 7
- 239000003814 drug Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- HOOWCUZPEFNHDT-UHFFFAOYSA-N DHPG Natural products OC(=O)C(N)C1=CC(O)=CC(O)=C1 HOOWCUZPEFNHDT-UHFFFAOYSA-N 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 238000012423 maintenance Methods 0.000 description 5
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000007908 dry granulation Methods 0.000 description 3
- 238000005469 granulation Methods 0.000 description 3
- 230000003179 granulation Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- LQIAZOCLNBBZQK-UHFFFAOYSA-N 1-(1,2-Diphosphanylethyl)pyrrolidin-2-one Chemical compound PCC(P)N1CCCC1=O LQIAZOCLNBBZQK-UHFFFAOYSA-N 0.000 description 2
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 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 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 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 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012628 flowing agent Substances 0.000 description 2
- 230000006870 function Effects 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
- 239000008103 glucose Substances 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- STFSJTPVIIDAQX-LTRPLHCISA-M sodium;(e)-4-octadecoxy-4-oxobut-2-enoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOC(=O)\C=C\C([O-])=O STFSJTPVIIDAQX-LTRPLHCISA-M 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003892 tartrate salts Chemical class 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
- DEXRDMVBOUGLGT-UHFFFAOYSA-N (3-oxo-1,2-dihydroinden-5-yl) n-ethyl-n-methylcarbamate Chemical compound CCN(C)C(=O)OC1=CC=C2CCC(=O)C2=C1 DEXRDMVBOUGLGT-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
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 241000416162 Astragalus gummifer Species 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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010048650 Cholinesterase inhibition Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920002785 Croscarmellose sodium 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
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 238000010268 HPLC based assay Methods 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
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- 208000025966 Neurological disease Diseases 0.000 description 1
- MHQJUHSHQGQVTM-HNENSFHCSA-N Octadecyl fumarate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)\C=C/C(O)=O MHQJUHSHQGQVTM-HNENSFHCSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000220010 Rhode Species 0.000 description 1
- 229910002054 SYLOID® 244 FP SILICA Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- 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
- 229920001615 Tragacanth Polymers 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
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229940023476 agar Drugs 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
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- 229910000278 bentonite Inorganic materials 0.000 description 1
- 229940092782 bentonite Drugs 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
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- 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
- 238000007907 direct compression Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
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- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 238000011020 pilot scale process Methods 0.000 description 1
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- 229940069328 povidone Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229940071138 stearyl fumarate Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 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
- A61K31/16—Amides, e.g. hydroxamic acids
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65647705P | 2005-02-24 | 2005-02-24 | |
| US60/656,477 | 2005-02-24 | ||
| PCT/US2006/006636 WO2006091836A1 (en) | 2005-02-24 | 2006-02-24 | Formulations of ladostigil tartrate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2600603A1 true CA2600603A1 (en) | 2006-08-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002600603A Abandoned CA2600603A1 (en) | 2005-02-24 | 2006-02-24 | Formulations of ladostigil tartrate |
Country Status (7)
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| US (2) | US8022104B2 (enExample) |
| EP (1) | EP1848417A1 (enExample) |
| JP (1) | JP2008531594A (enExample) |
| AU (1) | AU2006216509B8 (enExample) |
| CA (1) | CA2600603A1 (enExample) |
| IL (1) | IL185420A0 (enExample) |
| WO (1) | WO2006091836A1 (enExample) |
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| WO2006091836A1 (en) * | 2005-02-24 | 2006-08-31 | Teva Pharmaceutical Industries, Ltd. | Formulations of ladostigil tartrate |
| US20070093549A1 (en) * | 2005-09-28 | 2007-04-26 | Judith Aronhime | Methods for preparation of ladostigil tartrate crystalline form A1 |
| US7491847B2 (en) * | 2005-11-17 | 2009-02-17 | Teva Pharmaceutical Industries, Ltd. | Methods for isolating propargylated aminoindans |
| JP2009518433A (ja) * | 2005-12-09 | 2009-05-07 | イッサム リサーチ ディベロップメント カンパニー オブ ザ ヘブライ ユニバーシティー オブ エルサレム | 神経保護用の低用量ラドスチギルの使用 |
| US20070135518A1 (en) * | 2005-12-09 | 2007-06-14 | Marta Weinstock-Rosin | Use of low-dose ladostigil for neuroprotection |
| TW200744576A (en) | 2006-02-24 | 2007-12-16 | Teva Pharma | Propargylated aminoindans, processes for preparation, and uses thereof |
| WO2007126898A2 (en) * | 2006-03-31 | 2007-11-08 | Teva Pharmaceutical Industries, Ltd. | Use of ladostigil for the treatment of schizophrenia |
| WO2012059920A1 (en) * | 2010-11-02 | 2012-05-10 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Ladostigil dosage regime |
| WO2013118126A1 (en) | 2012-02-12 | 2013-08-15 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Ladostigil therapy for immunomodulation |
| WO2013182625A1 (en) * | 2012-06-08 | 2013-12-12 | Actavis Group Ptc Ehf | Pharmaceutical formulation with propargylamine compound |
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| US1534864A (en) * | 1919-12-19 | 1925-04-21 | Hazel Atlas Glass Co | Apparatus for tempering glassware |
| US2026165A (en) * | 1934-08-01 | 1935-12-31 | Libbey Owens Ford Glass Co | Process and apparatus for producing case hardened glass |
| US3903297A (en) | 1973-11-01 | 1975-09-02 | Upjohn Co | Method of treatment and prophylaxis of gastric hypersecretion and gastric and duodenal ulcers using prostaglandin analogs |
| US4086263A (en) * | 1976-11-17 | 1978-04-25 | Ppg Industries, Inc. | Shipping rack having spacer strips attached thereto |
| US4488192A (en) * | 1982-05-28 | 1984-12-11 | International Business Machines Corporation | Cooling arrangement for hermetically sealed disk files |
| US5744500A (en) | 1990-01-03 | 1998-04-28 | Teva Pharmaceutical Industries, Ltd. | Use of R-enantiomer of N-propargyl-1-aminoindan, salts, and compositions thereof |
| IL92952A (en) | 1990-01-03 | 1994-06-24 | Teva Pharma | R-enantiomers of n-propargyl-1-aminoindan compounds, their preparation and pharmaceutical compositions containing them |
| EP0738149B1 (en) | 1994-01-10 | 2006-11-29 | Teva Pharmaceutical Industries, Ltd. | 1-aminoindan derivatives and compositions thereof |
| FI100397B (fi) * | 1995-10-24 | 1997-11-28 | Glassrobots Oy | Lämmönsiirtomenetelmä lasilevyjen taivutusuunissa ja taivutusuuni |
| CN1183090A (zh) * | 1996-03-21 | 1998-05-27 | 彼得·利瑟 | 玻璃钢化方法及系统 |
| FR2747112B1 (fr) * | 1996-04-03 | 1998-05-07 | Commissariat Energie Atomique | Dispositif de transport d'objets plats et procede de transfert de ces objets entre ledit dispositif et une machine de traitement |
| CA2275425C (en) | 1996-12-18 | 2009-08-04 | Michael Chorev | Aminoindan derivatives |
| AU5620998A (en) | 1996-12-18 | 1998-07-15 | Technion Research & Development Foundation Ltd. | Phenylethylamine derivatives |
| US6251938B1 (en) | 1996-12-18 | 2001-06-26 | Teva Pharmaceutical Industries, Ltd., | Phenylethylamine derivatives |
| CA2276150A1 (en) | 1996-12-30 | 1998-07-09 | Steven D. Young | Inhibitors of farnesyl-protein transferase |
| JPH1179389A (ja) * | 1997-09-16 | 1999-03-23 | Mitsui Eng & Shipbuild Co Ltd | 基板ガラス検査加工システム |
| JPH1179388A (ja) * | 1997-09-16 | 1999-03-23 | Mitsui Eng & Shipbuild Co Ltd | ガラス類枚葉処理装置 |
| TW444275B (en) * | 1998-01-13 | 2001-07-01 | Toshiba Corp | Processing device, laser annealing device, laser annealing method, manufacturing device and substrate manufacturing device for panel display |
| AU2003219913A1 (en) | 2002-02-27 | 2003-09-09 | Teva Pharmaceutical Industries, Ltd. | Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective mao inhibitors |
| US20040010038A1 (en) | 2002-02-27 | 2004-01-15 | Eran Blaugrund | Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective MAO inhibitors |
| GB0322140D0 (en) * | 2003-09-22 | 2003-10-22 | Pfizer Ltd | Combinations |
| EP2433626B1 (en) | 2003-11-25 | 2015-11-04 | Technion Research & Development Foundation Ltd. | Compositions and methods for treatment of cardiovascular disorders and diseases |
| CA2566204A1 (en) | 2004-05-14 | 2005-12-01 | The Johns Hopkins University | Method for improving cognitive function by co-administration of a gabab receptor antagonist and an acetylcholinesterase inhibitor |
| US7335685B2 (en) | 2005-02-24 | 2008-02-26 | Teva Pharmaceutical Industries, Ltd. | Crystals of ladostigil tartrate, methods of production and pharmaceutical compositions thereof |
| WO2006091836A1 (en) | 2005-02-24 | 2006-08-31 | Teva Pharmaceutical Industries, Ltd. | Formulations of ladostigil tartrate |
| WO2006130726A2 (en) | 2005-06-01 | 2006-12-07 | Teva Pharmaceutical Industries, Ltd. | Use of ladostigil for the treatment of multiple sclerosis |
| US20070135518A1 (en) | 2005-12-09 | 2007-06-14 | Marta Weinstock-Rosin | Use of low-dose ladostigil for neuroprotection |
| JP2009518433A (ja) | 2005-12-09 | 2009-05-07 | イッサム リサーチ ディベロップメント カンパニー オブ ザ ヘブライ ユニバーシティー オブ エルサレム | 神経保護用の低用量ラドスチギルの使用 |
| TW200744576A (en) | 2006-02-24 | 2007-12-16 | Teva Pharma | Propargylated aminoindans, processes for preparation, and uses thereof |
| WO2007126898A2 (en) | 2006-03-31 | 2007-11-08 | Teva Pharmaceutical Industries, Ltd. | Use of ladostigil for the treatment of schizophrenia |
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2006
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- 2006-02-24 JP JP2007557195A patent/JP2008531594A/ja not_active Withdrawn
- 2006-02-24 CA CA002600603A patent/CA2600603A1/en not_active Abandoned
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2007
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2011
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Also Published As
| Publication number | Publication date |
|---|---|
| US20060189685A1 (en) | 2006-08-24 |
| JP2008531594A (ja) | 2008-08-14 |
| US20110301234A1 (en) | 2011-12-08 |
| WO2006091836A1 (en) | 2006-08-31 |
| WO2006091836A8 (en) | 2007-04-12 |
| EP1848417A1 (en) | 2007-10-31 |
| IL185420A0 (en) | 2008-08-07 |
| AU2006216509B8 (en) | 2012-11-01 |
| US8022104B2 (en) | 2011-09-20 |
| WO2006091836A9 (en) | 2006-10-26 |
| AU2006216509B2 (en) | 2012-05-31 |
| AU2006216509A1 (en) | 2006-08-31 |
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