PT106142B - Processo para a preparação de brometo de tiotrópio - Google Patents
Processo para a preparação de brometo de tiotrópio Download PDFInfo
- Publication number
- PT106142B PT106142B PT106142A PT10614212A PT106142B PT 106142 B PT106142 B PT 106142B PT 106142 A PT106142 A PT 106142A PT 10614212 A PT10614212 A PT 10614212A PT 106142 B PT106142 B PT 106142B
- Authority
- PT
- Portugal
- Prior art keywords
- process according
- tiotropium bromide
- solvent
- acetone
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 79
- 230000008569 process Effects 0.000 title claims abstract description 67
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 title abstract description 34
- 238000002360 preparation method Methods 0.000 title abstract description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 99
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 87
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 239000012442 inert solvent Substances 0.000 claims abstract description 13
- 238000002425 crystallisation Methods 0.000 claims abstract description 9
- 230000008025 crystallization Effects 0.000 claims abstract description 9
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 3
- FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 claims abstract 4
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims abstract 2
- 239000000047 product Substances 0.000 claims description 42
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 claims description 36
- 229960000257 tiotropium bromide Drugs 0.000 claims description 36
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 15
- 239000002245 particle Substances 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 11
- 239000000725 suspension Substances 0.000 claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- -1 n-heptane Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 6
- 238000005809 transesterification reaction Methods 0.000 claims description 6
- 239000012267 brine Substances 0.000 claims description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 239000012296 anti-solvent Substances 0.000 claims description 3
- 150000004292 cyclic ethers Chemical class 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
- 239000003610 charcoal Substances 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 3
- 238000001816 cooling Methods 0.000 claims 2
- 230000003247 decreasing effect Effects 0.000 claims 2
- 238000009413 insulation Methods 0.000 claims 2
- 238000007069 methylation reaction Methods 0.000 claims 2
- 238000001953 recrystallisation Methods 0.000 claims 2
- 238000001694 spray drying Methods 0.000 claims 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- KFKKXDNPLASYMH-UHFFFAOYSA-N n-ethylethanamine;oxalic acid Chemical compound CC[NH2+]CC.CC[NH2+]CC.[O-]C(=O)C([O-])=O KFKKXDNPLASYMH-UHFFFAOYSA-N 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- FIMXSEMBHGTNKT-UPGAHCIJSA-N scopine Chemical compound C([C@@H]1N2C)C(O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-UPGAHCIJSA-N 0.000 claims 1
- FIMXSEMBHGTNKT-RZVDLVGDSA-N scopine Chemical compound C([C@@H]1N2C)[C@H](O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-RZVDLVGDSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 description 33
- 239000000706 filtrate Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 229940110309 tiotropium Drugs 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
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- 150000004682 monohydrates Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
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- 239000002002 slurry Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 101150035983 str1 gene Proteins 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- QCYOIFVBYZNUNW-UHFFFAOYSA-N 2-(dimethylazaniumyl)propanoate Chemical compound CN(C)C(C)C(O)=O QCYOIFVBYZNUNW-UHFFFAOYSA-N 0.000 description 1
- CPLJMYOQYRCCBY-UHFFFAOYSA-N 2-Propylfuran Chemical compound CCCC1=CC=CO1 CPLJMYOQYRCCBY-UHFFFAOYSA-N 0.000 description 1
- HGBFVOSZYVRIHY-UHFFFAOYSA-N 2-cyanoprop-2-enamide Chemical compound NC(=O)C(=C)C#N HGBFVOSZYVRIHY-UHFFFAOYSA-N 0.000 description 1
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 description 1
- BPBQIKALCXYXID-UHFFFAOYSA-N 3-oxopropanoyl bromide Chemical compound BrC(=O)CC=O BPBQIKALCXYXID-UHFFFAOYSA-N 0.000 description 1
- MSVRGYOYISBGTH-UHFFFAOYSA-N 4-methoxy-2-methylbenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(C)=C1 MSVRGYOYISBGTH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920013663 Acetose Polymers 0.000 description 1
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- 241001167018 Aroa Species 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- KVOGSWGGFBTZAK-UHFFFAOYSA-N BrC1=CC=CS1.Br Chemical compound BrC1=CC=CS1.Br KVOGSWGGFBTZAK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 108010091326 Cryoglobulins Proteins 0.000 description 1
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- 101000601394 Homo sapiens Neuroendocrine convertase 2 Proteins 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
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- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
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- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
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- FRCCEHPWNOQAEU-UHFFFAOYSA-N heptachlor Chemical compound ClC1=C(Cl)C2(Cl)C3C=CC(Cl)C3C1(Cl)C2(Cl)Cl FRCCEHPWNOQAEU-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001509 metal bromide Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001936 parietal effect Effects 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 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
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT106142A PT106142B (pt) | 2012-02-10 | 2012-02-10 | Processo para a preparação de brometo de tiotrópio |
| CA2863772A CA2863772C (en) | 2012-02-10 | 2013-02-08 | Process for preparing tiotropium bromide |
| US14/377,271 US9090607B2 (en) | 2012-02-10 | 2013-02-08 | Process for preparing tiotropium bromide |
| BR112014019736-9A BR112014019736B1 (pt) | 2012-02-10 | 2013-02-08 | Processo para preparar brometo de tiotrópio |
| MX2014009568A MX352587B (es) | 2012-02-10 | 2013-02-08 | Procedimiento para la preparacion de bromuro de tiotropio. |
| PL13704817.9T PL2814827T3 (pl) | 2012-02-10 | 2013-02-08 | Sposób otrzymywania bromku tiotropiowego |
| NZ628768A NZ628768A (en) | 2012-02-10 | 2013-02-08 | Process for preparing tiotropium bromide |
| RU2014136706A RU2634715C2 (ru) | 2012-02-10 | 2013-02-08 | Способ получения тиотропия бромида |
| EP13704817.9A EP2814827B1 (en) | 2012-02-10 | 2013-02-08 | Process for preparing tiotropium bromide |
| JP2014556130A JP6118826B2 (ja) | 2012-02-10 | 2013-02-08 | 臭化チオトロピウムの調製方法 |
| HUE13704817A HUE029401T2 (en) | 2012-02-10 | 2013-02-08 | Process for the preparation of tiotropium bromide |
| CN201380008885.3A CN104144928B (zh) | 2012-02-10 | 2013-02-08 | 制备噻托溴铵的方法 |
| PCT/GB2013/000050 WO2013117886A1 (en) | 2012-02-10 | 2013-02-08 | Process for preparing tiotropium bromide |
| AU2013217467A AU2013217467B2 (en) | 2012-02-10 | 2013-02-08 | Process for preparing tiotropium bromide |
| SG11201404781QA SG11201404781QA (en) | 2012-02-10 | 2013-02-08 | Process for preparing tiotropium bromide |
| ES13704817.9T ES2592555T3 (es) | 2012-02-10 | 2013-02-08 | Procedimiento de preparación de bromuro de tiotropio |
| IN7390DEN2014 IN2014DN07390A (enExample) | 2012-02-10 | 2013-02-08 | |
| KR1020147024718A KR102011326B1 (ko) | 2012-02-10 | 2013-02-08 | 티오트로피움 브로마이드의 제조방법 |
| PH12014501771A PH12014501771B1 (en) | 2012-02-10 | 2014-08-06 | Process for preparing tiotropium bromide |
| IL234011A IL234011A (en) | 2012-02-10 | 2014-08-07 | Process for the preparation of Teotropium bromide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT106142A PT106142B (pt) | 2012-02-10 | 2012-02-10 | Processo para a preparação de brometo de tiotrópio |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT106142A PT106142A (pt) | 2013-08-12 |
| PT106142B true PT106142B (pt) | 2014-07-18 |
Family
ID=47722310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT106142A PT106142B (pt) | 2012-02-10 | 2012-02-10 | Processo para a preparação de brometo de tiotrópio |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US9090607B2 (enExample) |
| EP (1) | EP2814827B1 (enExample) |
| JP (1) | JP6118826B2 (enExample) |
| KR (1) | KR102011326B1 (enExample) |
| CN (1) | CN104144928B (enExample) |
| AU (1) | AU2013217467B2 (enExample) |
| BR (1) | BR112014019736B1 (enExample) |
| CA (1) | CA2863772C (enExample) |
| ES (1) | ES2592555T3 (enExample) |
| HU (1) | HUE029401T2 (enExample) |
| IL (1) | IL234011A (enExample) |
| IN (1) | IN2014DN07390A (enExample) |
| MX (1) | MX352587B (enExample) |
| NZ (1) | NZ628768A (enExample) |
| PH (1) | PH12014501771B1 (enExample) |
| PL (1) | PL2814827T3 (enExample) |
| PT (1) | PT106142B (enExample) |
| RU (1) | RU2634715C2 (enExample) |
| SG (1) | SG11201404781QA (enExample) |
| WO (1) | WO2013117886A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9108962B2 (en) | 2005-12-19 | 2015-08-18 | Sicor, Inc. | Forms of tiotropium bromide and processes for preparation thereof |
| EP2897955B1 (en) * | 2012-09-11 | 2019-11-06 | Bilgic, Mahmut | New tiotropium bromide crystalline form |
| CN104557905B (zh) * | 2013-10-16 | 2018-02-23 | 天津金耀集团有限公司 | 一种噻托溴铵中间体的制备方法 |
| KR20170019544A (ko) | 2015-08-11 | 2017-02-22 | 삼성디스플레이 주식회사 | 곡면 액정표시장치 및 이의 제조방법 |
| CN105807524B (zh) * | 2016-05-30 | 2019-04-16 | 京东方科技集团股份有限公司 | 阵列基板、显示面板及显示装置 |
| PT109740B (pt) * | 2016-11-14 | 2020-07-30 | Hovione Farmaciencia Sa | Processo para a preparação de brometo de umeclidínio |
| WO2018154596A1 (en) * | 2017-02-22 | 2018-08-30 | Gbr Laboratories Pvt. Ltd. | Process for synthesis of tiotropium bromide monohydrate |
| PT115583B (pt) | 2019-06-17 | 2022-05-02 | Hovione Farm S A | Processo contínuo para a preparação de medicamentos anticolinérgicos |
| CN114890997A (zh) * | 2022-04-20 | 2022-08-12 | 江苏联环药业股份有限公司 | 一种抗胆碱能药物噻格溴铵的制备工艺 |
Citations (5)
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|---|---|---|---|---|
| CA2620142A1 (en) * | 2005-12-19 | 2007-07-05 | Sicor Inc. | Pure and stable tiotropium bromide |
| CA2627729A1 (en) * | 2005-12-19 | 2007-07-05 | Sicor Inc. | Novel forms of tiotropium bromide and processes for preparation thereof |
| US20070167480A1 (en) * | 2005-12-19 | 2007-07-19 | Sicor Inc. | Pure and stable tiotropium bromide |
| US20080051582A1 (en) * | 2006-07-10 | 2008-02-28 | Sicor Inc. | Process for the preparation of tiotropium bromide |
| CN101331128A (zh) * | 2005-12-19 | 2008-12-24 | 西科尔公司 | 噻托溴铵的新形式及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US648632A (en) | 1898-05-16 | 1900-05-01 | John A Parker | Composite board. |
| DE3931041C2 (de) | 1989-09-16 | 2000-04-06 | Boehringer Ingelheim Kg | Ester von Thienylcarbonsäuren mit Aminoalkoholen, ihre Quaternierungsprodukte, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| US6908928B2 (en) | 2000-10-12 | 2005-06-21 | Bi Pharma Kg. | Crystalline tiotropium bromide monohydrate, processes for the preparation thereof, and pharmaceutical compositions |
| DE10064816A1 (de) | 2000-12-22 | 2002-06-27 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung eines Anticholinergikums |
| GB0100753D0 (en) | 2001-01-11 | 2001-02-21 | Bate Matthew | Data system |
| EP1401445B1 (de) * | 2001-06-22 | 2006-08-23 | Boehringer Ingelheim Pharma GmbH & Co.KG | Kristallines anticholinergikum, verfahren zu dessen herstellung und dessen verwendung zur herstellung eines arzneimittels |
| DE10200943A1 (de) | 2002-01-12 | 2003-07-24 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von Scopinestern |
| DE10212264A1 (de) * | 2002-03-20 | 2003-10-02 | Boehringer Ingelheim Pharma | Kristallines Mikronisat, Verfahren zu dessen Herstellung und dessen Verwendung zur Herstellung eines Arzneimittels |
| CA2545825A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| RU2417224C2 (ru) | 2005-05-02 | 2011-04-27 | Бёрингер Ингельхайм Интернациональ Гмбх | Новые кристаллические формы тиотропийбромида |
| RU2007144531A (ru) | 2005-05-02 | 2009-06-10 | БЕРИНГЕР ИНГЕЛЬХАЙМ ИНТЕРНАЦИОНАЛЬ ГмбХ (DE) | Новые кристаллические формы тиотропийбромида |
| EP1940441A4 (en) | 2005-08-19 | 2010-01-27 | Ironwood Pharmaceuticals Inc | COMPOSITIONS AND METHODS FOR TREATING GASTROINTESTINAL DISORDERS |
| DE102005059602A1 (de) | 2005-12-14 | 2007-06-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Mikronisierung |
| RU2453547C2 (ru) * | 2005-12-19 | 2012-06-20 | Сикор Инк. | Новые формы тиотропия бромида и способы их получения |
| EP1953156A1 (de) | 2007-01-29 | 2008-08-06 | Boehringer Ingelheim Pharma GmbH & Co. KG | Verfahren zur Herstellung von Scopiniumsalzen |
| SI2240477T1 (sl) | 2008-01-10 | 2015-02-27 | Generics (Uk) Limited | Nov postopek za pripravo estrov skopina |
| TW201020247A (en) * | 2008-11-06 | 2010-06-01 | Gruenenthal Gmbh | Substituierte disulfonamide |
| JP5822831B2 (ja) | 2009-08-07 | 2015-11-24 | ジェネリクス・［ユーケー］・リミテッド | チオトロピウム臭化物の無水物 |
| WO2011015884A1 (en) * | 2009-08-07 | 2011-02-10 | Generics [Uk] Limited | Process to prepare scopine esters |
| CN101863885B (zh) * | 2010-06-03 | 2012-05-30 | 南京金丹呈医药技术有限公司 | 一种噻托溴铵的制备方法 |
-
2012
- 2012-02-10 PT PT106142A patent/PT106142B/pt active IP Right Grant
-
2013
- 2013-02-08 AU AU2013217467A patent/AU2013217467B2/en not_active Ceased
- 2013-02-08 SG SG11201404781QA patent/SG11201404781QA/en unknown
- 2013-02-08 MX MX2014009568A patent/MX352587B/es active IP Right Grant
- 2013-02-08 ES ES13704817.9T patent/ES2592555T3/es active Active
- 2013-02-08 IN IN7390DEN2014 patent/IN2014DN07390A/en unknown
- 2013-02-08 CA CA2863772A patent/CA2863772C/en active Active
- 2013-02-08 KR KR1020147024718A patent/KR102011326B1/ko not_active Expired - Fee Related
- 2013-02-08 NZ NZ628768A patent/NZ628768A/en not_active IP Right Cessation
- 2013-02-08 BR BR112014019736-9A patent/BR112014019736B1/pt not_active IP Right Cessation
- 2013-02-08 JP JP2014556130A patent/JP6118826B2/ja not_active Expired - Fee Related
- 2013-02-08 EP EP13704817.9A patent/EP2814827B1/en active Active
- 2013-02-08 WO PCT/GB2013/000050 patent/WO2013117886A1/en not_active Ceased
- 2013-02-08 PL PL13704817.9T patent/PL2814827T3/pl unknown
- 2013-02-08 RU RU2014136706A patent/RU2634715C2/ru active
- 2013-02-08 US US14/377,271 patent/US9090607B2/en active Active
- 2013-02-08 HU HUE13704817A patent/HUE029401T2/en unknown
- 2013-02-08 CN CN201380008885.3A patent/CN104144928B/zh not_active Expired - Fee Related
-
2014
- 2014-08-06 PH PH12014501771A patent/PH12014501771B1/en unknown
- 2014-08-07 IL IL234011A patent/IL234011A/en active IP Right Grant
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