CA2620142A1 - Bromure de tiotropium pur et stable - Google Patents

Bromure de tiotropium pur et stable Download PDF

Info

Publication number: CA2620142A1
Authority: CA; Canada
Prior art keywords: tiotropium bromide; solvate; acid; eluent; glycolic acid
Prior art date: 2005-12-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002620142A

Other languages

English (en)

Inventor

Roberta Volonte

Nicola Diulgheroff

Francesca Scarpitta

Alessandro Pontiroli

Roberto Casalone

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sicor Inc

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

2005-12-19

Filing date

2006-12-19

Publication date

2007-07-05

2006-12-19 Application filed by Individual filed Critical Individual

2007-07-05 Publication of CA2620142A1 publication Critical patent/CA2620142A1/fr

Status Abandoned legal-status Critical Current

Links

229960000257 tiotropium bromide Drugs 0.000 title claims abstract description 194
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 title claims abstract description 192
238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 92
239000012453 solvate Substances 0.000 claims abstract description 87
FVEJUHUCFCAYRP-UHFFFAOYSA-N 2-hydroxy-2,2-dithiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(O)(C(=O)O)C1=CC=CS1 FVEJUHUCFCAYRP-UHFFFAOYSA-N 0.000 claims abstract description 66
239000000203 mixture Substances 0.000 claims abstract description 59
238000004519 manufacturing process Methods 0.000 claims abstract description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 159
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 68
238000000034 method Methods 0.000 claims description 65
239000003480 eluent Substances 0.000 claims description 54
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 41
239000002904 solvent Substances 0.000 claims description 40
239000000725 suspension Substances 0.000 claims description 37
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 33
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 32
150000007524 organic acids Chemical class 0.000 claims description 28
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 18
239000000546 pharmaceutical excipient Substances 0.000 claims description 18
-1 sopropanolate Chemical compound 0.000 claims description 17
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 16
239000008194 pharmaceutical composition Substances 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
238000001514 detection method Methods 0.000 claims description 13
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 13
238000010438 heat treatment Methods 0.000 claims description 11
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims description 8
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 8
239000011976 maleic acid Substances 0.000 claims description 8
235000019260 propionic acid Nutrition 0.000 claims description 8
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 7
239000011975 tartaric acid Substances 0.000 claims description 7
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 6
238000005259 measurement Methods 0.000 claims description 6
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims description 6
235000006408 oxalic acid Nutrition 0.000 claims description 6
235000002906 tartaric acid Nutrition 0.000 claims description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
238000001816 cooling Methods 0.000 claims description 5
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 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 3
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
238000009472 formulation Methods 0.000 abstract description 5
239000002253 acid Substances 0.000 description 37
229960000583 acetic acid Drugs 0.000 description 35
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
235000011054 acetic acid Nutrition 0.000 description 33
239000007787 solid Substances 0.000 description 28
235000019441 ethanol Nutrition 0.000 description 25
239000000243 solution Substances 0.000 description 25
229940110309 tiotropium Drugs 0.000 description 21
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 19
238000002425 crystallisation Methods 0.000 description 17
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
238000002360 preparation method Methods 0.000 description 11
239000000047 product Substances 0.000 description 11
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
239000007788 liquid Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002775 capsule Substances 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
239000003826 tablet Substances 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
229960004275 glycolic acid Drugs 0.000 description 8
239000008187 granular material Substances 0.000 description 8
229940093915 gynecological organic acid Drugs 0.000 description 8
150000007529 inorganic bases Chemical class 0.000 description 8
150000002825 nitriles Chemical class 0.000 description 8
235000005985 organic acids Nutrition 0.000 description 8
229920002472 Starch Polymers 0.000 description 7
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229940032147 starch Drugs 0.000 description 7
235000019698 starch Nutrition 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000001913 cellulose Substances 0.000 description 6
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
239000003085 diluting agent Substances 0.000 description 6
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
FIMXSEMBHGTNKT-RZVDLVGDSA-N scopine Chemical class C([C@@H]1N2C)[C@H](O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-RZVDLVGDSA-N 0.000 description 6
235000002639 sodium chloride Nutrition 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
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 5
239000008186 active pharmaceutical agent Substances 0.000 description 5
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 5
239000000969 carrier Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000001530 fumaric acid Substances 0.000 description 5
239000012535 impurity Substances 0.000 description 5
239000008101 lactose Substances 0.000 description 5
239000003495 polar organic solvent Substances 0.000 description 5
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VPJFFOQGKSJBAY-UHFFFAOYSA-N scopine di(2-thienyl) glycolate Chemical compound C1C(C2C3O2)N(C)C3CC1OC(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 VPJFFOQGKSJBAY-UHFFFAOYSA-N 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000005995 Aluminium silicate Substances 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
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 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229920002125 Sokalan® Polymers 0.000 description 4
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VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 3
241000220479 Acacia Species 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
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239000007971 pharmaceutical suspension Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
CKRORYDHXIRZCH-UHFFFAOYSA-N phosphoric acid;dihydrate Chemical compound O.O.OP(O)(O)=O CKRORYDHXIRZCH-UHFFFAOYSA-N 0.000 description 1
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229960000540 polacrilin potassium Drugs 0.000 description 1
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
WVWZXTJUCNEUAE-UHFFFAOYSA-M potassium;1,2-bis(ethenyl)benzene;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O.C=CC1=CC=CC=C1C=C WVWZXTJUCNEUAE-UHFFFAOYSA-M 0.000 description 1
229940069328 povidone Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
235000010409 propane-1,2-diol alginate Nutrition 0.000 description 1
239000000770 propane-1,2-diol alginate Substances 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 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
229960001790 sodium citrate Drugs 0.000 description 1
239000001540 sodium lactate Substances 0.000 description 1
235000011088 sodium lactate Nutrition 0.000 description 1
229940005581 sodium lactate Drugs 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
229940045902 sodium stearyl fumarate Drugs 0.000 description 1
DQHNAVOVODVIMG-RGECMCKFSA-M spiriva Chemical compound [Br-].C([C@@H]1[N+]([C@H](C2)[C@@H]3[C@H]1O3)(C)C)C2OC(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 DQHNAVOVODVIMG-RGECMCKFSA-M 0.000 description 1
229940046810 spiriva Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000013112 stability test Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004274 stearic acid Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
MQLXPRBEAHBZTK-SEINRUQRSA-M tiotropium bromide hydrate Chemical compound O.[Br-].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 MQLXPRBEAHBZTK-SEINRUQRSA-M 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 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
235000019731 tricalcium phosphate Nutrition 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
229940057977 zinc stearate Drugs 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
- C07D451/02—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
- 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
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
- 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
- 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
- A61P11/06—Antiasthmatics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Pulmonology (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Emergency Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA002620142A 2005-12-19 2006-12-19 Bromure de tiotropium pur et stable Abandoned CA2620142A1 (fr)

Applications Claiming Priority (25)

Application Number	Priority Date	Filing Date	Title
US75267205P	2005-12-19	2005-12-19
US60/752,672		2005-12-19
US75453005P	2005-12-27	2005-12-27
US60/754,530		2005-12-27
US76143706P	2006-01-23	2006-01-23
US60/761,437		2006-01-23
US77405106P	2006-02-15	2006-02-15
US60/774,051		2006-02-15
US78031006P	2006-03-07	2006-03-07
US60/780,310		2006-03-07
US83023106P	2006-07-10	2006-07-10
US60/830,231		2006-07-10
US83218906P	2006-07-20	2006-07-20
US60/832,189		2006-07-20
US83520106P	2006-08-03	2006-08-03
US83520006P	2006-08-03	2006-08-03
US60/835,200		2006-08-03
US60/835,201		2006-08-03
US83603706P	2006-08-07	2006-08-07
US60/836,037		2006-08-07
US85122306P	2006-10-12	2006-10-12
US60/851,223		2006-10-12
US85274006P	2006-10-18	2006-10-18
US60/852,740		2006-10-18
PCT/US2006/048690 WO2007075838A2 (fr)	2005-12-19	2006-12-19	Bromure de tiotropium pur et stable

Publications (1)

Publication Number	Publication Date
CA2620142A1 true CA2620142A1 (fr)	2007-07-05

Family

ID=38105786

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002620142A Abandoned CA2620142A1 (fr)	2005-12-19	2006-12-19	Bromure de tiotropium pur et stable

Country Status (9)

Country	Link
EP (1)	EP1966196A2 (fr)
JP (1)	JP2008530251A (fr)
KR (1)	KR20080079586A (fr)
CN (1)	CN101360744A (fr)
CA (1)	CA2620142A1 (fr)
IL (1)	IL188178A0 (fr)
MX (1)	MX2007009987A (fr)
TW (1)	TW200734333A (fr)
WO (1)	WO2007075838A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT106142A (pt) *	2012-02-10	2013-08-12	Hovione Farmaciencia S A	Processo para a preparação de brometo de tiotrópio

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2768553C (fr)	2009-08-07	2016-08-02	Generics [Uk] Limited	Anhydrate de bromure de tiotropium
WO2011015883A1 (fr) *	2009-08-07	2011-02-10	Generics [Uk] Limited	Solvate de dichlorométhane du bromure de tiotropium et son utilisation
WO2011095800A2 (fr) *	2010-02-02	2011-08-11	Generics [Uk] Limited	Procédés analytiques
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
TR201101897A2 (tr) *	2011-02-28	2012-09-21	Bi̇lgi̇ç Mahmut	Tiotropyum bromür içeren kristal madde
CZ304368B6 (cs)	2011-11-28	2014-04-02	Zentiva, K.S.	Směsný solvát tiotropium bromidu a způsob jeho přípravy
CN103130798B (zh) *	2011-11-30	2015-12-02	连云港润众制药有限公司	噻托溴铵的结晶
EP2789611A1 (fr) *	2013-04-08	2014-10-15	Cerbios-Pharma S.A.	Formules cristallines de bromure de tiotropium

Family Cites Families (6)

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Publication number	Priority date	Publication date	Assignee	Title
AP1712A (en) *	2000-10-12	2007-01-24	Boehringer Ingelheim Pharma	Novel tiotropium-containing inhalation powder
AU2002214996B2 (en) *	2000-10-12	2007-03-15	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Crystalline monohydrate, method for producing the same and the use thereof in the production of a medicament
DE10064816A1 (de) *	2000-12-22	2002-06-27	Boehringer Ingelheim Pharma	Verfahren zur Herstellung eines Anticholinergikums
DK1682543T3 (da) *	2003-11-03	2010-12-13	Boehringer Ingelheim Int	Fremgangsmåde til fremstilling af nye tiotropiumsalte
KR20080012932A (ko) *	2005-05-02	2008-02-12	베링거 인겔하임 인터내셔날 게엠베하	티오트로퓸 브로마이드의 신규한 결정형
EP1879888A2 (fr) *	2005-05-02	2008-01-23	Boehringer Ingelheim International GmbH	Formes cristallines de bromure de tiotropium

2006
- 2006-12-19 JP JP2007556440A patent/JP2008530251A/ja active Pending
- 2006-12-19 MX MX2007009987A patent/MX2007009987A/es not_active Application Discontinuation
- 2006-12-19 KR KR1020077018779A patent/KR20080079586A/ko not_active Withdrawn
- 2006-12-19 EP EP06845924A patent/EP1966196A2/fr not_active Withdrawn
- 2006-12-19 WO PCT/US2006/048690 patent/WO2007075838A2/fr not_active Ceased
- 2006-12-19 CA CA002620142A patent/CA2620142A1/fr not_active Abandoned
- 2006-12-19 TW TW095147753A patent/TW200734333A/zh unknown
- 2006-12-19 CN CNA2006800476882A patent/CN101360744A/zh active Pending
2007
- 2007-12-17 IL IL188178A patent/IL188178A0/en unknown

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT106142A (pt) *	2012-02-10	2013-08-12	Hovione Farmaciencia S A	Processo para a preparação de brometo de tiotrópio
PT106142B (pt) *	2012-02-10	2014-07-18	Hovione Farmaci Ncia S A	Processo para a preparação de brometo de tiotrópio

Also Published As

Publication number	Publication date
MX2007009987A (es)	2007-10-02
IL188178A0 (en)	2008-03-20
EP1966196A2 (fr)	2008-09-10
CN101360744A (zh)	2009-02-04
KR20080079586A (ko)	2008-09-01
TW200734333A (en)	2007-09-16
WO2007075838A3 (fr)	2007-08-16
JP2008530251A (ja)	2008-08-07
WO2007075838A2 (fr)	2007-07-05

Legal Events

Date	Code	Title	Description
2010-12-20	FZDE	Discontinued

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US9181268B2 (en)	2015-11-10	Anhydrate of tiotropium bromide
US20070167480A1 (en)	2007-07-19	Pure and stable tiotropium bromide
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US9108962B2 (en)	2015-08-18	Forms of tiotropium bromide and processes for preparation thereof
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KR20080021818A (ko)	2008-03-07	페놀도팜 메실레이트 결정형
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JP2008526780A (ja)	2008-07-24	ドルゾルアミド塩酸塩の非晶質および結晶質の形態およびそれらを製造する方法