JP2003531173A - ゾルピデムヘミタートレイト - Google Patents
ゾルピデムヘミタートレイトInfo
- Publication number
- JP2003531173A JP2003531173A JP2001577956A JP2001577956A JP2003531173A JP 2003531173 A JP2003531173 A JP 2003531173A JP 2001577956 A JP2001577956 A JP 2001577956A JP 2001577956 A JP2001577956 A JP 2001577956A JP 2003531173 A JP2003531173 A JP 2003531173A
- Authority
- JP
- Japan
- Prior art keywords
- zolpidem hemitartrate
- zolpidem
- hemitartrate
- particles
- microns
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- VXRDAMSNTXUHFX-CEAXSRTFSA-N zolpidem tartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1.N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 VXRDAMSNTXUHFX-CEAXSRTFSA-N 0.000 title claims abstract description 422
- 238000004519 manufacturing process Methods 0.000 claims abstract description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 140
- 238000000034 method Methods 0.000 claims description 100
- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 claims description 69
- 229960001475 zolpidem Drugs 0.000 claims description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- 239000002245 particle Substances 0.000 claims description 47
- 239000007787 solid Substances 0.000 claims description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- 239000002002 slurry Substances 0.000 claims description 34
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 30
- 238000002441 X-ray diffraction Methods 0.000 claims description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 21
- JHGHLTNIQXXXNV-UHFFFAOYSA-N 2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetic acid Chemical compound C1=CC(C)=CC=C1C1=C(CC(O)=O)N2C=C(C)C=CC2=N1 JHGHLTNIQXXXNV-UHFFFAOYSA-N 0.000 claims description 20
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 20
- 239000012453 solvate Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 16
- 206010022437 insomnia Diseases 0.000 claims description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000003937 drug carrier Substances 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- 150000004683 dihydrates Chemical class 0.000 claims description 9
- 239000011877 solvent mixture Substances 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 238000005660 chlorination reaction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 150000004682 monohydrates Chemical class 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 150000004685 tetrahydrates Chemical class 0.000 claims description 5
- 150000004684 trihydrates Chemical class 0.000 claims description 5
- -1 zolpidic acid halide Chemical class 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 4
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 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 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 239000006184 cosolvent Substances 0.000 claims 2
- 239000012429 reaction media Substances 0.000 claims 2
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 239000006163 transport media Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 42
- 238000002411 thermogravimetry Methods 0.000 description 25
- 239000000047 product Substances 0.000 description 19
- 238000003109 Karl Fischer titration Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
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- 230000004580 weight loss Effects 0.000 description 10
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- 150000001875 compounds Chemical class 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
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- 239000003814 drug Substances 0.000 description 7
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- 238000003795 desorption Methods 0.000 description 5
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- 229940079593 drug Drugs 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000004455 differential thermal analysis Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000004677 hydrates Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- VXRDAMSNTXUHFX-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n,n-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1.N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 VXRDAMSNTXUHFX-UHFFFAOYSA-N 0.000 description 3
- 229940094070 ambien Drugs 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000001358 L(+)-tartaric acid Substances 0.000 description 2
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 2
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-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
- 229920000881 Modified starch Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
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- 239000011248 coating agent Substances 0.000 description 2
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- 239000000498 cooling water Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004807 desolvation Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 238000009505 enteric coating Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
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- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- 239000008109 sodium starch glycolate Substances 0.000 description 2
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- 125000003944 tolyl group Chemical group 0.000 description 2
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- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- 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
- CTTJWXVQRJUJQW-UHFFFAOYSA-N 2,2-dioctyl-3-sulfobutanedioic acid Chemical compound CCCCCCCCC(C(O)=O)(C(C(O)=O)S(O)(=O)=O)CCCCCCCC CTTJWXVQRJUJQW-UHFFFAOYSA-N 0.000 description 1
- NSJOHWXCJYNOSF-UHFFFAOYSA-N 2-imidazo[1,2-a]pyridin-3-ylacetamide Chemical compound C1=CC=CN2C(CC(=O)N)=CN=C21 NSJOHWXCJYNOSF-UHFFFAOYSA-N 0.000 description 1
- XWSCOGPKWVNQSV-UHFFFAOYSA-N 5-bromo-2,3-dichloropyridine Chemical compound ClC1=CC(Br)=CN=C1Cl XWSCOGPKWVNQSV-UHFFFAOYSA-N 0.000 description 1
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- 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
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- PUPKPAZSFZOLOR-UHFFFAOYSA-N n,n-dimethylformamide;toluene Chemical compound CN(C)C=O.CC1=CC=CC=C1 PUPKPAZSFZOLOR-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 102000054765 polymorphisms of proteins Human genes 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000004620 sleep latency Effects 0.000 description 1
- 230000004622 sleep time Effects 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
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 229960005111 zolpidem tartrate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Other Liquid Machine Or Engine Such As Wave Power Use (AREA)
- Suspension Of Electric Lines Or Cables (AREA)
- Amplifiers (AREA)
- Supply Devices, Intensifiers, Converters, And Telemotors (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19929800P | 2000-04-24 | 2000-04-24 | |
| US60/199,298 | 2000-04-24 | ||
| US20602500P | 2000-05-22 | 2000-05-22 | |
| US60/206,025 | 2000-05-22 | ||
| US22536400P | 2000-08-14 | 2000-08-14 | |
| US60/225,364 | 2000-08-14 | ||
| PCT/US2001/013175 WO2001080857A1 (en) | 2000-04-24 | 2001-04-24 | Zolpidem hemitartrate |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006033099A Division JP2006137778A (ja) | 2000-04-24 | 2006-02-09 | ゾルピデムヘミタートレイト |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003531173A true JP2003531173A (ja) | 2003-10-21 |
| JP2003531173A5 JP2003531173A5 (https=) | 2005-12-22 |
Family
ID=27394001
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001577956A Withdrawn JP2003531173A (ja) | 2000-04-24 | 2001-04-24 | ゾルピデムヘミタートレイト |
| JP2006033099A Pending JP2006137778A (ja) | 2000-04-24 | 2006-02-09 | ゾルピデムヘミタートレイト |
| JP2006177160A Pending JP2006249105A (ja) | 2000-04-24 | 2006-06-27 | ゾルピデムヘミタートレイト |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006033099A Pending JP2006137778A (ja) | 2000-04-24 | 2006-02-09 | ゾルピデムヘミタートレイト |
| JP2006177160A Pending JP2006249105A (ja) | 2000-04-24 | 2006-06-27 | ゾルピデムヘミタートレイト |
Country Status (21)
| Country | Link |
|---|---|
| US (8) | US20020077332A1 (https=) |
| EP (1) | EP1292304B1 (https=) |
| JP (3) | JP2003531173A (https=) |
| KR (1) | KR20030069796A (https=) |
| AT (4) | ATE338550T1 (https=) |
| AU (2) | AU5721301A (https=) |
| CA (1) | CA2406982A1 (https=) |
| CZ (1) | CZ20023775A3 (https=) |
| DE (7) | DE04010651T1 (https=) |
| DK (1) | DK1292304T3 (https=) |
| ES (4) | ES2239558T3 (https=) |
| HR (1) | HRP20020909A2 (https=) |
| HU (1) | HUP0300701A2 (https=) |
| IL (1) | IL152411A0 (https=) |
| NZ (1) | NZ522015A (https=) |
| PL (1) | PL358548A1 (https=) |
| PT (3) | PT1475093E (https=) |
| SE (1) | SE5292304T3 (https=) |
| SK (1) | SK16372002A3 (https=) |
| WO (1) | WO2001080857A1 (https=) |
| YU (1) | YU79402A (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009510163A (ja) * | 2005-10-03 | 2009-03-12 | マリンクロッド・インコーポレイテッド | ヘミ酒石酸および酒石酸ゾルピデム多形の製造方法 |
| WO2011115069A1 (ja) * | 2010-03-19 | 2011-09-22 | 第一三共株式会社 | 結晶の網羅的探索 |
| JP2016510752A (ja) * | 2013-03-06 | 2016-04-11 | ヤンセン ファーマシューティカ エヌ．ベー． | ヒスタミンｈ４受容体のベンゾイミダゾール−２−イルピリミジンモジュレータ |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001284322A1 (en) | 2000-08-29 | 2002-03-13 | Ranbaxy Laboratories Limited | Synthesis of n,n-dimethyl-3-(4-methyl) benzoyl propionamide, a key intermediate of zolpidem |
| US6869970B2 (en) | 2002-02-04 | 2005-03-22 | Novartis Ag | Crystalline salt forms of valsartan |
| ES2320758T3 (es) | 2002-12-18 | 2009-05-28 | Mallinckrodt Inc. | Sintesis de heteroaril acetamidas. |
| WO2004087703A1 (en) * | 2003-03-12 | 2004-10-14 | Sun Pharmaceutical Industries Limited | Process for the preparation of n,n,6-trimethyl-2-(4-methylphenyl)-imidazo[1,2-a]pyridine-3-acetamide |
| EP1660496A1 (en) * | 2003-07-31 | 2006-05-31 | Ranbaxy Laboratories Limited | Process for the synthesis of zolpidem |
| EP1715853A4 (en) * | 2004-02-17 | 2012-07-18 | Transcept Pharmaceuticals Inc | COMPOSITIONS FOR THE DISTRIBUTION OF HYPNOTICS IN THE FIELD OF MUNICHCHLEIMHÄUTE AND USE METHOD THEREOF |
| US20080262025A1 (en) * | 2004-07-16 | 2008-10-23 | Yatendra Kumar | Processes for the Preparation of Zolpidem and its Hemitartrate |
| US20070225322A1 (en) * | 2005-05-25 | 2007-09-27 | Transoral Pharmaceuticals, Inc. | Compositions and methods for treating middle-of-the night insomnia |
| US20070123562A1 (en) * | 2005-05-25 | 2007-05-31 | Transoral Pharmaceuticals, Inc. | Compositions and methods for treating middle-of-the-night insomnia |
| US20070287740A1 (en) * | 2005-05-25 | 2007-12-13 | Transcept Pharmaceuticals, Inc. | Compositions and methods of treating middle-of-the night insomnia |
| ES2336142T3 (es) * | 2005-08-19 | 2010-04-08 | Aventis Pharmaceuticals Inc. | Combinacion de un agente hipnotico y un compuesto sustituido, con bis arilo y heteroarilo y aplicacion terapeutica del mismo. |
| KR20080034475A (ko) * | 2005-08-19 | 2008-04-21 | 아벤티스 파마슈티칼스 인크. | 수면제 및ｒ(＋)-알파-(2,3-디메톡시-페닐)-1-[2-(4-플루오로페닐)에틸]-4-피페리딘메탄올의 복합물 및 이의 치료학적 용도 |
| EP1948134A2 (en) * | 2005-10-17 | 2008-07-30 | Mallinckrodt, Inc. | Polymorph transformation of zolpidem in tablet matrix |
| US20070098788A1 (en) * | 2005-10-28 | 2007-05-03 | Gore Subhash P | Non-benzodiazepine hypnotic compositions |
| PL2007752T3 (pl) | 2006-03-31 | 2011-02-28 | Janssen Pharmaceutica Nv | Benzoimidazol-2-ilopirymidyny i pirazyny jako modulatory receptora histaminowego H4 |
| US20080132535A1 (en) * | 2006-11-30 | 2008-06-05 | Transcept Pharmaceuticals, Inc. | Stabilized Zolpidem Pharmaceutical Compositions |
| US20080145425A1 (en) * | 2006-12-15 | 2008-06-19 | Pliva Research & Development Limited | Pharmaceutical composition of zolpidem |
| US20100029942A1 (en) * | 2008-06-30 | 2010-02-04 | Sergio Cesco-Cancian | Process for the preparation of benzoimidazol-2-yl pyrimidine derivatives |
| US9371311B2 (en) | 2008-06-30 | 2016-06-21 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyrimidine derivatives |
| CA3140959A1 (en) | 2009-11-27 | 2011-06-03 | Genzyme Corporation | An amorphous and a crystalline form of genz 112638 hemitartrate as inhibitor of glucosylceramide synthase |
| CN116283958B (zh) * | 2021-12-03 | 2026-02-24 | 山东新时代药业有限公司 | 唑吡坦共晶体及其制备方法 |
| CN116283957A (zh) * | 2021-12-03 | 2023-06-23 | 山东新时代药业有限公司 | 唑吡坦水合物及其制备方法 |
| CN117907368A (zh) * | 2024-01-27 | 2024-04-19 | 鲁南贝特制药有限公司 | 一种酒石酸唑吡坦药用晶型d中晶型a、e的定量测定方法 |
| CN118750459B (zh) * | 2024-07-22 | 2025-04-01 | 常州市武进中医医院 | 一种酒石酸唑吡坦片及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4151273A (en) * | 1974-10-31 | 1979-04-24 | The Regents Of The University Of California | Increasing the absorption rate of insoluble drugs |
| FR2408345A1 (fr) * | 1976-11-30 | 1979-06-08 | Besins Jean Louis | Nouvelle composition a action anti-conceptionnelle |
| US4302446A (en) * | 1979-10-02 | 1981-11-24 | Bristol-Myers Company | Pharmaceutical compositions |
| IT1130924B (it) * | 1980-03-06 | 1986-06-18 | Secifarma Spa | Procedimento per la preparazione di spironolattone micronizzato |
| DE3018940A1 (de) * | 1980-05-17 | 1981-11-26 | Hoechst Ag, 6000 Frankfurt | Verwendung eines vinylchlorid-pfropf-copolymerisates in der plastisolverarbeitung |
| FR2492382A1 (fr) * | 1980-10-22 | 1982-04-23 | Synthelabo | Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique |
| FR2525601A1 (fr) * | 1982-04-21 | 1983-10-28 | Synthelabo | Derives d'imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique |
| US4675323A (en) * | 1985-08-06 | 1987-06-23 | Synthelabo | Imidazo(1,2-a)quinoline derivatives useful as anxiolytic agents |
| SE457326B (sv) * | 1986-02-14 | 1988-12-19 | Lejus Medical Ab | Foerfarande foer framstaellning av en snabbt soenderfallande kaerna innehaallande bl a mikrokristallin cellulosa |
| FR2600650B1 (fr) * | 1986-06-27 | 1988-09-09 | Synthelabo | Procede de preparation d'imidazopyridines et composes intermediaires |
| FR2606410B1 (fr) * | 1986-11-07 | 1989-02-24 | Synthelabo | Imidazopyridines, leur preparation et leur application en therapeutique |
| ES2026666T3 (es) * | 1987-03-27 | 1992-05-01 | Synthelabo | Procedimiento para preparar derivados de imidazopiridinas. |
| US5271944A (en) * | 1991-04-05 | 1993-12-21 | Biofor, Ltd. | Pharmacologically enhanced formulations |
| IT1276522B1 (it) * | 1995-04-07 | 1997-10-31 | Elena Benincasa | Uso dello zolpidem per il trattamento terapeudico di sindromi neuropsichiatriche associate a disfunsione e di circuiti neurali dei |
| ATE242241T1 (de) * | 1999-03-25 | 2003-06-15 | Synthon Bv | Imidazopyridinderivate und verfahren zu ihrer herstellung |
| DE60020814T2 (de) * | 1999-03-25 | 2006-05-04 | Synthon B.V. | Zolpidem salze |
| AU6474200A (en) * | 1999-12-13 | 2001-06-18 | Sumika Fine Chemicals Co., Ltd. | Process for the preparation of a pyridinemethanol compound |
-
2001
- 2001-04-24 ES ES04010651T patent/ES2239558T3/es not_active Expired - Lifetime
- 2001-04-24 PL PL01358548A patent/PL358548A1/xx not_active Application Discontinuation
- 2001-04-24 AT AT04010651T patent/ATE338550T1/de not_active IP Right Cessation
- 2001-04-24 KR KR1020027014220A patent/KR20030069796A/ko not_active Ceased
- 2001-04-24 AT AT05001922T patent/ATE348613T1/de not_active IP Right Cessation
- 2001-04-24 PT PT04010651T patent/PT1475093E/pt unknown
- 2001-04-24 HU HU0300701A patent/HUP0300701A2/hu unknown
- 2001-04-24 AU AU5721301A patent/AU5721301A/xx active Pending
- 2001-04-24 DE DE04010651T patent/DE04010651T1/de active Pending
- 2001-04-24 ES ES05001922T patent/ES2277301T3/es not_active Expired - Lifetime
- 2001-04-24 CA CA002406982A patent/CA2406982A1/en not_active Abandoned
- 2001-04-24 CZ CZ20023775A patent/CZ20023775A3/cs unknown
- 2001-04-24 YU YU79402A patent/YU79402A/sh unknown
- 2001-04-24 AU AU2001257213A patent/AU2001257213B2/en not_active Ceased
- 2001-04-24 ES ES01930705T patent/ES2248321T3/es not_active Expired - Lifetime
- 2001-04-24 PT PT04010435T patent/PT1473036E/pt unknown
- 2001-04-24 JP JP2001577956A patent/JP2003531173A/ja not_active Withdrawn
- 2001-04-24 DK DK01930705T patent/DK1292304T3/da active
- 2001-04-24 WO PCT/US2001/013175 patent/WO2001080857A1/en not_active Ceased
- 2001-04-24 DE DE60125429T patent/DE60125429T2/de not_active Expired - Fee Related
- 2001-04-24 SK SK1637-2002A patent/SK16372002A3/sk not_active Application Discontinuation
- 2001-04-24 DE DE60122944T patent/DE60122944T2/de not_active Expired - Fee Related
- 2001-04-24 AT AT04010435T patent/ATE335481T1/de not_active IP Right Cessation
- 2001-04-24 HR HR20020909A patent/HRP20020909A2/hr not_active Application Discontinuation
- 2001-04-24 NZ NZ522015A patent/NZ522015A/en unknown
- 2001-04-24 PT PT05001922T patent/PT1541146E/pt unknown
- 2001-04-24 SE SE01930705T patent/SE5292304T3/xx unknown
- 2001-04-24 DE DE20122435U patent/DE20122435U1/de not_active Expired - Lifetime
- 2001-04-24 AT AT01930705T patent/ATE308324T1/de not_active IP Right Cessation
- 2001-04-24 IL IL15241101A patent/IL152411A0/xx unknown
- 2001-04-24 ES ES04010435T patent/ES2238941T3/es not_active Expired - Lifetime
- 2001-04-24 EP EP01930705A patent/EP1292304B1/en not_active Revoked
- 2001-04-24 DE DE60122216T patent/DE60122216T2/de not_active Expired - Fee Related
- 2001-04-24 DE DE04010435T patent/DE04010435T1/de active Pending
- 2001-04-24 US US09/841,025 patent/US20020077332A1/en not_active Abandoned
- 2001-04-24 DE DE60114617T patent/DE60114617T2/de not_active Expired - Fee Related
-
2004
- 2004-05-24 US US10/853,338 patent/US20040220212A1/en not_active Abandoned
- 2004-05-24 US US10/853,345 patent/US20040220213A1/en not_active Abandoned
- 2004-05-24 US US10/853,640 patent/US20040214859A1/en not_active Abandoned
- 2004-05-24 US US10/853,031 patent/US20040220210A1/en not_active Abandoned
- 2004-05-24 US US10/853,033 patent/US20040220211A1/en not_active Abandoned
- 2004-05-24 US US10/852,912 patent/US20040214858A1/en not_active Abandoned
-
2006
- 2006-02-09 JP JP2006033099A patent/JP2006137778A/ja active Pending
- 2006-06-27 JP JP2006177160A patent/JP2006249105A/ja active Pending
- 2006-10-25 US US11/588,122 patent/US20070037843A1/en not_active Abandoned
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009510163A (ja) * | 2005-10-03 | 2009-03-12 | マリンクロッド・インコーポレイテッド | ヘミ酒石酸および酒石酸ゾルピデム多形の製造方法 |
| WO2011115069A1 (ja) * | 2010-03-19 | 2011-09-22 | 第一三共株式会社 | 結晶の網羅的探索 |
| JP2016510752A (ja) * | 2013-03-06 | 2016-04-11 | ヤンセン ファーマシューティカ エヌ．ベー． | ヒスタミンｈ４受容体のベンゾイミダゾール−２−イルピリミジンモジュレータ |
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