UA68402C2 - Eletriptan hydrobromide monohydrate, pharmaceutical composition, method of treatment (variants), method for synthesis of eletriptan hydrobromide monohydrate (variants) and method for preparing anhydrous eletriptan hydrobromide - Google Patents
Eletriptan hydrobromide monohydrate, pharmaceutical composition, method of treatment (variants), method for synthesis of eletriptan hydrobromide monohydrate (variants) and method for preparing anhydrous eletriptan hydrobromide Download PDFInfo
- Publication number
- UA68402C2 UA68402C2 UA2001053569A UA2001053569A UA68402C2 UA 68402 C2 UA68402 C2 UA 68402C2 UA 2001053569 A UA2001053569 A UA 2001053569A UA 2001053569 A UA2001053569 A UA 2001053569A UA 68402 C2 UA68402 C2 UA 68402C2
- Authority
- UA
- Ukraine
- Prior art keywords
- eletriptan hydrobromide
- eletriptan
- monohydrate
- hydrobromide monohydrate
- item
- Prior art date
Links
- BORDVONYOHPTGR-JQDLGSOUSA-N 5-[2-(benzenesulfonyl)ethyl]-3-[[(2r)-1-methylpyrrolidin-2-yl]methyl]-1h-indole;hydrate;hydrobromide Chemical compound O.[Br-].C[N@H+]1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1 BORDVONYOHPTGR-JQDLGSOUSA-N 0.000 title claims abstract description 72
- 238000000034 method Methods 0.000 title claims abstract description 24
- 229960003470 eletriptan hydrobromide Drugs 0.000 title claims description 21
- UTINOWOSWSPFLJ-FSRHSHDFSA-N eletriptan hydrobromide Chemical compound Br.CN1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1 UTINOWOSWSPFLJ-FSRHSHDFSA-N 0.000 title claims description 20
- 238000011282 treatment Methods 0.000 title claims description 9
- 230000015572 biosynthetic process Effects 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 150000004682 monohydrates Chemical class 0.000 claims abstract description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 18
- 229960002472 eletriptan Drugs 0.000 claims description 17
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 14
- 208000019695 Migraine disease Diseases 0.000 claims description 13
- 206010027599 migraine Diseases 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 206010019233 Headaches Diseases 0.000 claims description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 6
- 231100000869 headache Toxicity 0.000 claims description 6
- 230000000306 recurrent effect Effects 0.000 claims description 6
- 108020003175 receptors Proteins 0.000 claims description 5
- 102000005962 receptors Human genes 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 206010009094 Chronic paroxysmal hemicrania Diseases 0.000 claims description 3
- 206010013654 Drug abuse Diseases 0.000 claims description 3
- 208000030814 Eating disease Diseases 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 235000014632 disordered eating Nutrition 0.000 claims description 3
- 229960001340 histamine Drugs 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 208000007777 paroxysmal Hemicrania Diseases 0.000 claims description 3
- 239000000952 serotonin receptor agonist Substances 0.000 claims description 3
- 208000011117 substance-related disease Diseases 0.000 claims description 3
- 208000019553 vascular disease Diseases 0.000 claims description 3
- 206010047700 Vomiting Diseases 0.000 claims description 2
- 230000008673 vomiting Effects 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 4
- 239000000556 agonist Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 108091005482 5-HT4 receptors Proteins 0.000 claims 1
- OTLDLQZJRFYOJR-LJQANCHMSA-N eletriptan Chemical compound CN1CCC[C@@H]1CC1=CN=C2[C]1C=C(CCS(=O)(=O)C=1C=CC=CC=1)C=C2 OTLDLQZJRFYOJR-LJQANCHMSA-N 0.000 claims 1
- 239000002895 emetic Substances 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- PWVXXGRKLHYWKM-LJQANCHMSA-N eletriptan Chemical compound CN1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1 PWVXXGRKLHYWKM-LJQANCHMSA-N 0.000 description 16
- 239000000725 suspension Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- -1 monohydrate eletriptan hydrobromide Chemical class 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 5
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 5
- 239000012730 sustained-release form Substances 0.000 description 5
- 238000001757 thermogravimetry curve Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000013268 sustained release Methods 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000013270 controlled release Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000009977 dual effect Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 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 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920002785 Croscarmellose sodium Polymers 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 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 2
- 239000000443 aerosol Substances 0.000 description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 229960001681 croscarmellose sodium Drugs 0.000 description 2
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- 238000001914 filtration Methods 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
- 229940057995 liquid paraffin Drugs 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 239000007909 solid dosage form Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 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
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- IYVZCNNIKYUHHM-WXMGBDCWSA-N OS(O)(=O)=O.CN1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1.CN1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1 Chemical compound OS(O)(=O)=O.CN1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1.CN1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1 IYVZCNNIKYUHHM-WXMGBDCWSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 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
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 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
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 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
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000004106 carminic acid Substances 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229940112141 dry powder inhaler Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000008387 emulsifying waxe Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000002638 palliative care Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000008063 pharmaceutical solvent Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000011321 prophylaxis Methods 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
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Nutrition Science (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
- Lasers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9825988.0A GB9825988D0 (en) | 1998-11-27 | 1998-11-27 | Indole derivatives |
| PCT/IB1999/001754 WO2000032589A1 (fr) | 1998-11-27 | 1999-11-01 | Monohydrate de bromhydrate d'eletriptan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA68402C2 true UA68402C2 (en) | 2004-08-16 |
Family
ID=10843140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001053569A UA68402C2 (en) | 1998-11-27 | 1999-01-11 | Eletriptan hydrobromide monohydrate, pharmaceutical composition, method of treatment (variants), method for synthesis of eletriptan hydrobromide monohydrate (variants) and method for preparing anhydrous eletriptan hydrobromide |
Country Status (53)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0018968D0 (en) * | 2000-08-02 | 2000-09-20 | Pfizer Ltd | Particulate composition |
| WO2004089365A1 (fr) | 2003-04-11 | 2004-10-21 | Pfizer Limited | Combinaison pharmaceutique a base d'eletriptan et de bicarbonate de sodium |
| GB0317229D0 (en) * | 2003-07-23 | 2003-08-27 | Pfizer Ltd | Improved process |
| US6927296B2 (en) | 2003-07-23 | 2005-08-09 | Pfizer Inc. | Process |
| US20080287519A1 (en) * | 2007-05-01 | 2008-11-20 | Marioara Mendelovici | Amorphous eletriptan hydrobromide and process for preparing it and other forms of eletriptan hydrobromide |
| US20080319205A1 (en) * | 2007-05-29 | 2008-12-25 | Roman Bednar | Process for preparing 5-bromo-3-[(R)-1-methyl-pyrrolidin-2-ylmethyl]-1H-indole |
| EP2225224A2 (fr) * | 2007-12-17 | 2010-09-08 | Actavis Group PTC EHF | Sel semioxalate innovant de l'élétriptan |
| US20120027816A1 (en) * | 2009-02-25 | 2012-02-02 | Actavis Group Ptc Ehf | Highly pure eletriptan or a pharmaceutically acceptable salt thereof substantially free of eletriptan n-oxide impurity |
| WO2010116386A2 (fr) * | 2009-04-08 | 2010-10-14 | Biophore India Pharmaceuticals Pvt. Ltd. | Nouveau polymorphe de bromhydrate d'életriptan et son procédé de fabrication |
| WO2011089614A1 (fr) * | 2010-01-19 | 2011-07-28 | Sms Pharmaceuticals Limited | Procédé de préparation de bromhydrate d'élétriptan ayant une forme α |
| WO2014063752A1 (fr) | 2012-10-26 | 2014-05-01 | Synthon Bv | Procédé de production de la forme cristalline alpha du bromhydrure d'élétriptan |
| CN103893112A (zh) * | 2012-12-31 | 2014-07-02 | 重庆圣华曦药业股份有限公司 | 氢溴酸依来曲普坦注射液 |
| CN107954947A (zh) * | 2016-10-14 | 2018-04-24 | 北京莱瑞森医药科技有限公司 | 沃替西汀氢溴酸盐晶型c及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3952741A (en) | 1975-01-09 | 1976-04-27 | Bend Research Inc. | Controlled release delivery system by an osmotic bursting mechanism |
| FR2624732B1 (fr) | 1987-12-21 | 1991-02-15 | Synthelabo | Formulation pharmaceutique a liberation prolongee |
| US5474784A (en) | 1990-03-02 | 1995-12-12 | British Technology Group Limited | Dispensing device |
| DE9190141U1 (de) | 1990-10-15 | 1993-07-15 | Pfizer Inc., New York, N.Y. | Indolderivate |
| US5545644A (en) * | 1990-10-15 | 1996-08-13 | Pfizer Inc. | Indole derivatives |
| US5464633A (en) | 1994-05-24 | 1995-11-07 | Jagotec Ag | Pharmaceutical tablets releasing the active substance after a definite period of time |
| GB9417310D0 (en) * | 1994-08-27 | 1994-10-19 | Pfizer Ltd | Therapeutic agents |
| GB9510223D0 (en) | 1995-05-20 | 1995-07-19 | Pfizer Ltd | Therapeutic agent |
| TW448172B (en) * | 1996-03-08 | 2001-08-01 | Pharmacia & Upjohn Co Llc | Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation |
| US5998462A (en) * | 1996-12-16 | 1999-12-07 | Allelix Biopharmaceuticals Inc. | 5-alkyl indole compounds |
| GB9704498D0 (en) * | 1997-03-05 | 1997-04-23 | Glaxo Wellcome Spa | Chemical compound |
| PL337803A1 (en) | 1997-07-03 | 2000-09-11 | Pfizer | Pharmaceutic agents containing eletriptane hemisulphate and caffeine |
-
1998
- 1998-11-27 GB GBGB9825988.0A patent/GB9825988D0/en not_active Ceased
-
1999
- 1999-01-11 UA UA2001053569A patent/UA68402C2/uk unknown
- 1999-11-01 EP EP99949292A patent/EP1135381B1/fr not_active Expired - Lifetime
- 1999-11-01 EA EA200100297A patent/EA003551B1/ru not_active IP Right Cessation
- 1999-11-01 ID IDW00200101132A patent/ID28802A/id unknown
- 1999-11-01 DE DE69919388T patent/DE69919388T2/de not_active Expired - Fee Related
- 1999-11-01 CZ CZ20011839A patent/CZ295472B6/cs not_active IP Right Cessation
- 1999-11-01 SK SK699-2001A patent/SK285774B6/sk unknown
- 1999-11-01 OA OA1200100103A patent/OA11671A/en unknown
- 1999-11-01 RS YUP-188/01A patent/RS50002B/sr unknown
- 1999-11-01 TR TR2001/01493T patent/TR200101493T2/xx unknown
- 1999-11-01 GE GEAP19995913A patent/GEP20043183B/en unknown
- 1999-11-01 EE EEP200100285A patent/EE04914B1/xx not_active IP Right Cessation
- 1999-11-01 IL IL14166399A patent/IL141663A/en not_active IP Right Cessation
- 1999-11-01 WO PCT/IB1999/001754 patent/WO2000032589A1/fr active IP Right Grant
- 1999-11-01 NZ NZ510055A patent/NZ510055A/en unknown
- 1999-11-01 ES ES99949292T patent/ES2224701T3/es not_active Expired - Lifetime
- 1999-11-01 CN CN998135798A patent/CN1131860C/zh not_active Expired - Fee Related
- 1999-11-01 CA CA002352392A patent/CA2352392C/fr not_active Expired - Fee Related
- 1999-11-01 AP APAP/P/2001/002149A patent/AP2001002149A0/en unknown
- 1999-11-01 KR KR10-2001-7006605A patent/KR100413739B1/ko not_active IP Right Cessation
- 1999-11-01 HU HU0105308A patent/HUP0105308A3/hu unknown
- 1999-11-01 PT PT99949292T patent/PT1135381E/pt unknown
- 1999-11-01 AT AT99949292T patent/ATE273300T1/de not_active IP Right Cessation
- 1999-11-01 PL PL99347928A patent/PL194503B1/pl unknown
- 1999-11-01 DK DK99949292T patent/DK1135381T3/da active
- 1999-11-01 AU AU62253/99A patent/AU754731B2/en not_active Ceased
- 1999-11-01 SI SI9930633T patent/SI1135381T1/xx unknown
- 1999-11-01 JP JP2000585231A patent/JP3777094B2/ja not_active Expired - Fee Related
- 1999-11-01 BR BR9915692-0A patent/BR9915692A/pt not_active Application Discontinuation
- 1999-11-02 TW TW088119069A patent/TWI246512B/zh not_active IP Right Cessation
- 1999-11-09 HN HN1999000196A patent/HN1999000196A/es unknown
- 1999-11-18 PA PA19998485701A patent/PA8485701A1/es unknown
- 1999-11-23 PE PE1999001178A patent/PE20001299A1/es not_active Application Discontinuation
- 1999-11-24 DZ DZ990248A patent/DZ2948A1/fr active
- 1999-11-24 CO CO99074057A patent/CO5150178A1/es unknown
- 1999-11-24 TN TNTNSN99221A patent/TNSN99221A1/fr unknown
- 1999-11-24 GC GCP1999381 patent/GC0000113A/xx active
- 1999-11-24 MA MA25854A patent/MA26708A1/fr unknown
- 1999-11-25 MY MYPI99005153A patent/MY124078A/en unknown
- 1999-11-25 AR ARP990106025A patent/AR024232A1/es not_active Application Discontinuation
- 1999-11-26 GT GT199900202A patent/GT199900202A/es unknown
- 1999-11-26 SV SV1999000204A patent/SV1999000204A/es not_active Application Discontinuation
- 1999-11-29 US US09/450,462 patent/US20020013358A1/en not_active Abandoned
- 1999-11-29 UY UY25823A patent/UY25823A1/es unknown
- 1999-11-30 UY UY25825A patent/UY25825A1/es unknown
-
2001
- 2001-02-27 IS IS5868A patent/IS2238B/is unknown
- 2001-03-13 CU CU20010065A patent/CU23269A3/es unknown
- 2001-03-14 CR CR6325A patent/CR6325A/xx not_active Application Discontinuation
- 2001-04-02 ZA ZA200102681A patent/ZA200102681B/xx unknown
- 2001-05-23 BG BG105539A patent/BG64706B1/bg unknown
- 2001-05-24 HR HR20010398 patent/HRP20010398B1/xx not_active IP Right Cessation
- 2001-05-25 NO NO20012584A patent/NO320798B1/no unknown
-
2002
- 2002-06-11 HK HK02104379.1A patent/HK1042898B/zh not_active IP Right Cessation
-
2003
- 2003-02-27 US US10/376,385 patent/US7238723B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2159241C2 (ru) | Соли производного индола против мигрени | |
| UA68402C2 (en) | Eletriptan hydrobromide monohydrate, pharmaceutical composition, method of treatment (variants), method for synthesis of eletriptan hydrobromide monohydrate (variants) and method for preparing anhydrous eletriptan hydrobromide | |
| JP2002510703A (ja) | 抗ウイルス性ベンズイミダゾール化合物の新規な結晶形 | |
| HU196775B (en) | Process for production of morfologically unique new modifications of famotidin and medical compositions containing such substances | |
| EA004510B1 (ru) | Полиморфная форма гемисульфата 3-(n-метил)-2(r)-пирролидинилметил-5-(2-фенилсульфонилэтил)-1h-индола | |
| EA004748B1 (ru) | Полиморфные формы 4-амино-6,7-диметокси-2-(5-метансульфонамидо-1,2,3,4-тетрагидроизохинолин-2-ил)-5-(2-пиридил) хиназолина и его мезилатной соли | |
| MXPA01005313A (en) | Eletriptan hydrobromide monohydrate | |
| RU2178789C2 (ru) | Новые полиморфные формы дигидрохлорида лесопитрона и их гидратные формы, способы получения и композиции на их основе |