DK1937642T3 - Crystals of sodium laquinimod and the process for its preparation - Google Patents
Crystals of sodium laquinimod and the process for its preparation Download PDFInfo
- Publication number
- DK1937642T3 DK1937642T3 DK06826297.1T DK06826297T DK1937642T3 DK 1937642 T3 DK1937642 T3 DK 1937642T3 DK 06826297 T DK06826297 T DK 06826297T DK 1937642 T3 DK1937642 T3 DK 1937642T3
- Authority
- DK
- Denmark
- Prior art keywords
- sodium
- laquinimod
- mixture
- volume
- laquinimod sodium
- Prior art date
Links
- 229960004577 laquinimod Drugs 0.000 title claims description 121
- GKWPCEFFIHSJOE-UHFFFAOYSA-N laquinimod Chemical compound OC=1C2=C(Cl)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC=C1 GKWPCEFFIHSJOE-UHFFFAOYSA-N 0.000 title claims description 120
- 238000000034 method Methods 0.000 title claims description 61
- 239000013078 crystal Substances 0.000 title claims description 24
- 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 title claims description 13
- 239000011734 sodium Substances 0.000 title claims description 13
- 229910052708 sodium Inorganic materials 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 62
- 239000000243 solution Substances 0.000 claims description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- 239000002245 particle Substances 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 239000007787 solid Substances 0.000 claims description 29
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 18
- 239000012535 impurity Substances 0.000 claims description 17
- 239000012296 anti-solvent Substances 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 229910052804 chromium Inorganic materials 0.000 claims description 12
- 239000011651 chromium Substances 0.000 claims description 12
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 10
- 229910001385 heavy metal Inorganic materials 0.000 claims description 10
- 229910052742 iron Inorganic materials 0.000 claims description 10
- 229910052759 nickel Inorganic materials 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 239000002775 capsule Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000011081 inoculation Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 238000001953 recrystallisation Methods 0.000 description 26
- 238000002425 crystallisation Methods 0.000 description 20
- 230000008025 crystallization Effects 0.000 description 20
- 239000000126 substance Substances 0.000 description 13
- 238000004090 dissolution Methods 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000009826 distribution Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000010899 nucleation Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
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- 229940088679 drug related substance Drugs 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
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- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
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- 239000006186 oral dosage form Substances 0.000 description 3
- 238000001878 scanning electron micrograph Methods 0.000 description 3
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- 229940032147 starch Drugs 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 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
- 239000003086 colorant Substances 0.000 description 2
- 238000001739 density measurement Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 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
- 238000002156 mixing Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 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
- 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
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 208000032116 Autoimmune Experimental Encephalomyelitis 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
- 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-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
- 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
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000220010 Rhode Species 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
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 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
- 230000001154 acute effect Effects 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
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 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
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000001514 detection method Methods 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
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
- 208000012997 experimental autoimmune encephalomyelitis Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- PAIDZDPOJWEZLX-UHFFFAOYSA-N methyl 5-chloro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxylate Chemical compound C1=CC=C2N(C)C(=O)C(C(=O)OC)=C(O)C2=C1Cl PAIDZDPOJWEZLX-UHFFFAOYSA-N 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002133 sample digestion Methods 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 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
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 238000012546 transfer Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003039 volatile agent Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72865705P | 2005-10-19 | 2005-10-19 | |
| PCT/US2006/040925 WO2007047863A2 (en) | 2005-10-19 | 2006-10-18 | Crystals of laquinimod sodium, and process for the manufacture thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK1937642T3 true DK1937642T3 (en) | 2014-12-15 |
Family
ID=37963287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK06826297.1T DK1937642T3 (en) | 2005-10-19 | 2006-10-18 | Crystals of sodium laquinimod and the process for its preparation |
Country Status (23)
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8314124B2 (en) | 2004-02-06 | 2012-11-20 | Active Biotech Ab | Crystalline salts of quinoline compounds and methods for preparing them |
| BRPI0617477A2 (pt) * | 2005-10-19 | 2011-07-26 | Teva Pharma | mistura de partÍculas cristalinas de laquinimod sàdica, composiÇço, processo de cristalizaÇço de laquinimod sàdica, laquinimod sàdica, e, processo para produzir uma composiÇço farmacÊutica |
| CN101466379B (zh) | 2006-06-12 | 2012-10-31 | 泰华制药工业有限公司 | 稳定的拉喹莫德的制剂 |
| WO2009082471A1 (en) * | 2007-12-20 | 2009-07-02 | Teva Pharmaceutical Industries, Ltd. | Stable laquinimod preparations |
| US8354428B2 (en) | 2008-07-01 | 2013-01-15 | Actavis Group Ptc Ehf | Solid state forms of laquinimod and its sodium salt |
| AU2009288108B2 (en) * | 2008-09-03 | 2013-10-17 | Teva Pharmaceutical Industries, Ltd. | 2-oxo-1,2-dihydro-quinoline modulators of immune function |
| WO2010070449A2 (en) | 2008-12-17 | 2010-06-24 | Actavis Group Ptc Ehf | Highly pure laquinimod or a pharmaceutically acceptable salt thereof |
| DE102009008851A1 (de) | 2009-02-13 | 2010-08-19 | Amw Gmbh | Transdermales System mit Immunmodulator |
| DE102010048788A1 (de) | 2009-02-13 | 2011-05-19 | Amw Gmbh | Transdermales System mit Immunmodulator |
| NZ597378A (en) | 2009-06-19 | 2014-08-29 | Teva Pharma | Treatment of multiple sclerosis with laquinimod |
| BR112012002124A2 (pt) * | 2009-07-30 | 2015-09-15 | Teva Pharma | tratamento da doença de crohn com laquinimode. |
| WO2011019375A1 (en) * | 2009-08-10 | 2011-02-17 | Teva Pharmaceutical Industries Ltd. | Treatment of bdnf-related disorders using laquinimod |
| DE102010026879A1 (de) | 2010-02-11 | 2011-08-11 | AMW GmbH, 83627 | Transdermales System mit Immunmodulator |
| EA201290860A1 (ru) * | 2010-03-03 | 2013-04-30 | Тева Фармасьютикал Индастриз Лтд. | Лечение ревматоидного артрита комбинацией лаквинимода и метотрексата |
| US20110217295A1 (en) * | 2010-03-03 | 2011-09-08 | Asi Haviv | Treatment of lupus arthritis using laquinimod |
| KR20130006640A (ko) | 2010-03-03 | 2013-01-17 | 테바 파마슈티컬 인더스트리즈 리미티드 | 라퀴니모드를 이용한 루푸스 신장염의 치료 |
| JP5934202B2 (ja) | 2010-07-09 | 2016-06-15 | テバ ファーマシューティカル インダストリーズ リミティド | ５−クロロ−４−ヒドロキシ−１−メチル−２−オキソ−ｎ−フェニル−１，２−ジヒドロキノリン−３−カルボキサミドと、その塩及びその使用 |
| AU2011274496B2 (en) * | 2010-07-09 | 2016-03-10 | Teva Pharmaceutical Industries Ltd. | Deuterated N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide, salts and uses thereof |
| US8865742B2 (en) | 2010-11-28 | 2014-10-21 | Mapi Pharma Ltd. | Intermediate compounds and processes for the preparation of quinoline derivatives such as Laquinimod sodium |
| SG11201401330YA (en) * | 2011-10-12 | 2014-05-29 | Teva Pharma | Treatment of multiple sclerosis with combination of laquinimod and fingolimod |
| WO2013116657A1 (en) | 2012-02-03 | 2013-08-08 | Teva Pharmaceutical Industries Ltd. | USE OF LAQUINIMOD FOR TREATING CROHN'S DISEASE PATIENTS WHO FAILED FIRST-LINE ANTI-TNFα THERAPY |
| MX2014009889A (es) * | 2012-02-16 | 2014-11-13 | Teva Pharma | N-etil-n-fenil-1,2-dihidro-4,5-di-hidroxi-1-metil-2-oxo-3-quinoli ncarboxamida, preparacion y usos de los mismos. |
| US20130259856A1 (en) | 2012-03-27 | 2013-10-03 | Teva Pharmaceutical Industries, Ltd. | Treatment of multiple sclerosis with combination of laquinimod and dimethyl fumarate |
| TW201350467A (zh) | 2012-05-08 | 2013-12-16 | Teva Pharma | Ｎ－乙基－４－羥基－１－甲基－５－（甲基（２，３，４，５，６－五羥基己基）胺基）－２－側氧－ｎ－苯基－１，２－二氫喹啉－３－甲醯胺 |
| TW201400117A (zh) | 2012-06-05 | 2014-01-01 | Teva Pharma | 使用拉喹莫德治療眼發炎疾病 |
| AR091706A1 (es) * | 2012-07-11 | 2015-02-25 | Teva Pharma | Formulaciones de laquinimod sin agentes alcalinizantes |
| TW201410244A (zh) | 2012-08-13 | 2014-03-16 | Teva Pharma | 用於治療ｇａｂａ媒介之疾病之拉喹莫德（ｌａｑｕｉｎｉｍｏｄ） |
| CN103626701A (zh) * | 2012-08-28 | 2014-03-12 | 天津药物研究院 | 一种制备喹啉衍生物的方法 |
| CN103626702A (zh) * | 2012-08-30 | 2014-03-12 | 天津药物研究院 | 一种制备喹啉酮衍生物的方法 |
| WO2014033954A1 (ja) | 2012-09-03 | 2014-03-06 | トヨタ自動車株式会社 | 衝突判定装置及び衝突判定方法 |
| EA201590788A1 (ru) | 2012-11-07 | 2015-12-30 | Тева Фармасьютикал Индастриз Лтд. | Аминные соли лахинимода |
| JP2016514162A (ja) * | 2013-03-14 | 2016-05-19 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドナトリウムの結晶およびその製造のための改善された方法 |
| WO2014152009A1 (en) | 2013-03-14 | 2014-09-25 | Teva Pharmaceutical Industries Ltd. | Transdermal formulations of laquinimod |
| TWI665190B (zh) | 2013-11-15 | 2019-07-11 | 阿克比治療有限公司 | ｛［５－（３－氯苯基）－３－羥基吡啶－２－羰基］胺基｝乙酸之固體型式，其組合物及用途 |
| HK1231413A1 (zh) | 2014-04-29 | 2017-12-22 | Teva Pharmaceutical Industries Ltd. | 用於治疗具有高残疾状况的复发-缓解型多发性硬化症(rrms)的患者的拉喹莫德 |
| JP7842983B2 (ja) * | 2021-02-25 | 2026-04-09 | 学校法人神戸学院 | 腸管吸収用補助剤及びその利用方法 |
| KR102876408B1 (ko) * | 2022-01-24 | 2025-10-24 | 한국과학기술원 | 입도가 조절된 헥사나이트로스틸벤 타입 iv의 제조방법 |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US613574A (en) * | 1898-11-01 | Feed-regulator | ||
| US3024257A (en) * | 1961-04-10 | 1962-03-06 | Frosst & Co Charles E | Stable preparations of alkali metal salts of estrone sulfate |
| FR2340735A1 (fr) * | 1976-02-11 | 1977-09-09 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
| IE52670B1 (en) * | 1981-03-03 | 1988-01-20 | Leo Ab | Heterocyclic carboxamides,compositions containing such compounds,and processes for their preparation |
| DE3437232A1 (de) * | 1984-10-10 | 1986-04-17 | Mack Chem Pharm | Stabilisierte injektionsloesungen von piroxicam |
| SE8902076D0 (sv) | 1989-06-09 | 1989-06-09 | Pharmacia Ab | Derivatives of quinoline-3-carboxanilide |
| HUT60458A (en) | 1991-02-01 | 1992-09-28 | Sandoz Ag | Process for producing benzyloxyphenyl derivatives and pharmaceutical compositions comprising same |
| DE4120646A1 (de) * | 1991-06-22 | 1992-12-24 | Bayer Ag | 7-isoindolinyl-chinolon- und naphthyridoncarbonsaeure-derivate |
| US5540934A (en) * | 1994-06-22 | 1996-07-30 | Touitou; Elka | Compositions for applying active substances to or through the skin |
| CH687615A5 (de) | 1994-09-07 | 1997-01-15 | R W Johnson Pharmaceutical Res | Tropen-Verpackung. |
| US5912349A (en) * | 1997-01-31 | 1999-06-15 | Pharmacia & Upjohn Company | Process for the preparation of roquinimex |
| US20030124187A1 (en) * | 1997-02-14 | 2003-07-03 | Smithkline Beecham Laboratoires Pharmaceutiques, | Pharmaceutical formulations comprising amoxycillin and clavulanate |
| CA2303867C (en) | 1997-09-19 | 2004-05-11 | Cosco, Inc. | Playyard |
| US6077851A (en) * | 1998-04-27 | 2000-06-20 | Active Biotech Ab | Quinoline derivatives |
| SE9801474D0 (sv) * | 1998-04-27 | 1998-04-27 | Active Biotech Ab | Quinoline Derivatives |
| SE9802549D0 (sv) | 1998-07-15 | 1998-07-15 | Active Biotech Ab | Quinoline derivatives |
| US6133285A (en) * | 1998-07-15 | 2000-10-17 | Active Biotech Ab | Quinoline derivatives |
| SE9802550D0 (sv) | 1998-07-15 | 1998-07-15 | Active Biotech Ab | Quinoline derivatives |
| US6121287A (en) * | 1998-07-15 | 2000-09-19 | Active Biotech Ab | Quinoline derivatives |
| EE200100660A (et) | 1999-06-07 | 2003-04-15 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Ravimvorm happe suhtes labiilsete toimeainete jaoks, toimeaine üksus, selle valmistamismeetod ja mikrokerake |
| PL199781B1 (pl) * | 1999-10-25 | 2008-10-31 | Active Biotech Ab | Nowe związki pochodne chinoliny, zastosowanie związków pochodnych chinoliny, zawierające je kompozycje farmaceutyczne i sposób ich wytwarzania |
| SE0002320D0 (sv) | 1999-10-25 | 2000-06-21 | Active Biotech Ab | Malignant tumors |
| JP2002031610A (ja) * | 2000-07-14 | 2002-01-31 | Ajinomoto Co Inc | 生体分子複合体の界面残基を同定する方法 |
| US6307050B1 (en) * | 2000-08-29 | 2001-10-23 | R. T. Alamo Venture I Llc | Method of synthesizing flosequinan from 4-fluoroanthranilic acid |
| US6802422B2 (en) * | 2000-12-12 | 2004-10-12 | Multi-Comp, Inc. | Sealed blister assembly |
| US6706733B2 (en) * | 2001-05-08 | 2004-03-16 | Dainippon Ink And Chemicals, Inc. | Quinolinone derivative formulation and its production method |
| US20030119826A1 (en) * | 2001-09-24 | 2003-06-26 | Pharmacia Corporation | Neuroprotective treatment methods using selective iNOS inhibitors |
| US6875869B2 (en) * | 2002-06-12 | 2005-04-05 | Active Biotech Ab | Process for the manufacture of quinoline derivatives |
| SE0201778D0 (sv) | 2002-06-12 | 2002-06-12 | Active Biotech Ab | Process for the manufacture of quinoline derivatives |
| US7560557B2 (en) * | 2002-06-12 | 2009-07-14 | Active Biotech Ag | Process for the manufacture of quinoline derivatives |
| EP1386926A1 (en) | 2002-07-29 | 2004-02-04 | Bioxtal | Methods for producing labelled recombinant polypeptides and uses thereof |
| ITMI20021726A1 (it) | 2002-08-01 | 2004-02-02 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| US7820145B2 (en) * | 2003-08-04 | 2010-10-26 | Foamix Ltd. | Oleaginous pharmaceutical and cosmetic foam |
| US7790197B2 (en) * | 2003-06-09 | 2010-09-07 | Warner-Lambert Company Llc | Pharmaceutical compositions of atorvastatin |
| US20040253305A1 (en) * | 2003-06-12 | 2004-12-16 | Luner Paul E. | Pharmaceutical compositions of atorvastatin |
| US20050271717A1 (en) * | 2003-06-12 | 2005-12-08 | Alfred Berchielli | Pharmaceutical compositions of atorvastatin |
| EP1694308A1 (en) | 2003-10-30 | 2006-08-30 | Lupin Ltd. | Stable formulations of ace inhibitors and methods for preparation thereof |
| US8314124B2 (en) * | 2004-02-06 | 2012-11-20 | Active Biotech Ab | Crystalline salts of quinoline compounds and methods for preparing them |
| SE0400235D0 (sv) | 2004-02-06 | 2004-02-06 | Active Biotech Ab | New composition containing quinoline compounds |
| BRPI0617477A2 (pt) * | 2005-10-19 | 2011-07-26 | Teva Pharma | mistura de partÍculas cristalinas de laquinimod sàdica, composiÇço, processo de cristalizaÇço de laquinimod sàdica, laquinimod sàdica, e, processo para produzir uma composiÇço farmacÊutica |
| CN101466379B (zh) | 2006-06-12 | 2012-10-31 | 泰华制药工业有限公司 | 稳定的拉喹莫德的制剂 |
| WO2009082471A1 (en) * | 2007-12-20 | 2009-07-02 | Teva Pharmaceutical Industries, Ltd. | Stable laquinimod preparations |
| US8354428B2 (en) | 2008-07-01 | 2013-01-15 | Actavis Group Ptc Ehf | Solid state forms of laquinimod and its sodium salt |
| AU2009288108B2 (en) | 2008-09-03 | 2013-10-17 | Teva Pharmaceutical Industries, Ltd. | 2-oxo-1,2-dihydro-quinoline modulators of immune function |
| NZ597378A (en) | 2009-06-19 | 2014-08-29 | Teva Pharma | Treatment of multiple sclerosis with laquinimod |
| BR112012002124A2 (pt) | 2009-07-30 | 2015-09-15 | Teva Pharma | tratamento da doença de crohn com laquinimode. |
| WO2011019375A1 (en) | 2009-08-10 | 2011-02-17 | Teva Pharmaceutical Industries Ltd. | Treatment of bdnf-related disorders using laquinimod |
| US20110217295A1 (en) | 2010-03-03 | 2011-09-08 | Asi Haviv | Treatment of lupus arthritis using laquinimod |
| KR20130006640A (ko) | 2010-03-03 | 2013-01-17 | 테바 파마슈티컬 인더스트리즈 리미티드 | 라퀴니모드를 이용한 루푸스 신장염의 치료 |
| EA201290860A1 (ru) | 2010-03-03 | 2013-04-30 | Тева Фармасьютикал Индастриз Лтд. | Лечение ревматоидного артрита комбинацией лаквинимода и метотрексата |
| JP5934202B2 (ja) | 2010-07-09 | 2016-06-15 | テバ ファーマシューティカル インダストリーズ リミティド | ５−クロロ−４−ヒドロキシ−１−メチル−２−オキソ−ｎ−フェニル−１，２−ジヒドロキノリン−３−カルボキサミドと、その塩及びその使用 |
| AU2011274496B2 (en) | 2010-07-09 | 2016-03-10 | Teva Pharmaceutical Industries Ltd. | Deuterated N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide, salts and uses thereof |
| US20120055072A1 (en) * | 2010-09-08 | 2012-03-08 | Rankin Sammy D | Directional guide for fishing lures |
| PE20140872A1 (es) | 2010-12-07 | 2014-08-09 | Teva Pharma | Uso de laquinimod para reducir la fatiga, mejorar el estado funcional y mejorar la calidad de vida en pacientes con esclerosis multiple |
-
2006
- 2006-10-18 BR BRPI0617477-9A patent/BRPI0617477A2/pt not_active Application Discontinuation
- 2006-10-18 CN CN200680039201.6A patent/CN101291911B/zh not_active Expired - Fee Related
- 2006-10-18 NZ NZ567088A patent/NZ567088A/en unknown
- 2006-10-18 DK DK06826297.1T patent/DK1937642T3/en active
- 2006-10-18 RU RU2008119456/04A patent/RU2415841C2/ru not_active IP Right Cessation
- 2006-10-18 CN CN2013102471796A patent/CN103333107A/zh active Pending
- 2006-10-18 NZ NZ592897A patent/NZ592897A/xx unknown
- 2006-10-18 WO PCT/US2006/040925 patent/WO2007047863A2/en not_active Ceased
- 2006-10-18 ZA ZA200803527A patent/ZA200803527B/xx unknown
- 2006-10-18 CA CA2625287A patent/CA2625287C/en not_active Expired - Fee Related
- 2006-10-18 SG SG10201508623RA patent/SG10201508623RA/en unknown
- 2006-10-18 SI SI200631860T patent/SI1937642T1/sl unknown
- 2006-10-18 UA UAA200806003A patent/UA92761C2/ru unknown
- 2006-10-18 AU AU2006304672A patent/AU2006304672B2/en not_active Ceased
- 2006-10-18 US US11/583,282 patent/US7884208B2/en not_active Expired - Fee Related
- 2006-10-18 EP EP06826297.1A patent/EP1937642B1/en active Active
- 2006-10-18 RS RS20140629A patent/RS53666B1/sr unknown
- 2006-10-18 HR HRP20141160TT patent/HRP20141160T1/hr unknown
- 2006-10-18 ES ES06826297.1T patent/ES2523762T3/es active Active
- 2006-10-18 CN CN201710533188.XA patent/CN107176923A/zh active Pending
- 2006-10-18 KR KR1020087011727A patent/KR101440982B1/ko not_active Expired - Fee Related
- 2006-10-18 JP JP2008536806A patent/JP5832716B2/ja not_active Expired - Fee Related
- 2006-10-18 PL PL06826297T patent/PL1937642T3/pl unknown
- 2006-10-18 EP EP13153698.9A patent/EP2687512A1/en not_active Withdrawn
- 2006-10-18 PT PT68262971T patent/PT1937642E/pt unknown
- 2006-10-19 AR ARP060104574A patent/AR056708A1/es unknown
-
2008
- 2008-03-13 IL IL190137A patent/IL190137A/en not_active IP Right Cessation
-
2011
- 2011-01-21 US US13/011,187 patent/US8673322B2/en not_active Expired - Fee Related
- 2011-01-21 US US13/011,233 patent/US8647646B2/en not_active Expired - Fee Related
-
2012
- 2012-12-19 JP JP2012277069A patent/JP2013100299A/ja not_active Withdrawn
-
2014
- 2014-02-20 US US14/185,470 patent/US20140171647A1/en not_active Abandoned
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2015
- 2015-07-31 JP JP2015152209A patent/JP2016020353A/ja active Pending
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