CN105601628A - 用于制备东莨菪醇酯的方法 - Google Patents
用于制备东莨菪醇酯的方法 Download PDFInfo
- Publication number
- CN105601628A CN105601628A CN201610056741.0A CN201610056741A CN105601628A CN 105601628 A CN105601628 A CN 105601628A CN 201610056741 A CN201610056741 A CN 201610056741A CN 105601628 A CN105601628 A CN 105601628A
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- CN
- China
- Prior art keywords
- aryl
- group
- alkynyl
- optional replacement
- tiotropium
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
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- 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 abstract description 34
- 229960000257 tiotropium bromide Drugs 0.000 claims abstract description 27
- 150000003839 salts Chemical group 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 8
- -1 alcohol ester Chemical class 0.000 claims description 39
- 239000002585 base Substances 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 229940110309 tiotropium Drugs 0.000 claims description 17
- 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 claims description 17
- 239000003513 alkali Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
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- 239000001257 hydrogen Substances 0.000 claims description 10
- 241001419717 Anisodus luridus Species 0.000 claims description 9
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- 125000002769 thiazolinyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
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- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
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- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
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- 229940102396 methyl bromide Drugs 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
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- 239000000376 reactant Substances 0.000 description 3
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
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- 230000035479 physiological effects, processes and functions Effects 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- BBBRAOXIMQHVCR-QYRWGYAXSA-N scopine hydrochloride Chemical compound Cl.C([C@@H]1N2C)C(O)C[C@@H]2[C@@H]2[C@H]1O2 BBBRAOXIMQHVCR-QYRWGYAXSA-N 0.000 description 2
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- 125000001544 thienyl group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 229940071648 metered dose inhaler Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229960001609 oxitropium bromide Drugs 0.000 description 1
- LCELQERNWLBPSY-KHSTUMNDSA-M oxitropium bromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CC)=CC=CC=C1 LCELQERNWLBPSY-KHSTUMNDSA-M 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN77KO2008 | 2008-01-10 | ||
| IN77/KOL/2008 | 2008-01-10 | ||
| CN2009801017774A CN101918401A (zh) | 2008-01-10 | 2009-01-09 | 用于制备东莨菪醇酯的新方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009801017774A Division CN101918401A (zh) | 2008-01-10 | 2009-01-09 | 用于制备东莨菪醇酯的新方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105601628A true CN105601628A (zh) | 2016-05-25 |
Family
ID=40451439
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610056741.0A Pending CN105601628A (zh) | 2008-01-10 | 2009-01-09 | 用于制备东莨菪醇酯的方法 |
| CN2009801017774A Pending CN101918401A (zh) | 2008-01-10 | 2009-01-09 | 用于制备东莨菪醇酯的新方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009801017774A Pending CN101918401A (zh) | 2008-01-10 | 2009-01-09 | 用于制备东莨菪醇酯的新方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20110028508A1 (enExample) |
| EP (1) | EP2240477B8 (enExample) |
| JP (2) | JP6087492B2 (enExample) |
| CN (2) | CN105601628A (enExample) |
| AU (1) | AU2009203579B2 (enExample) |
| CA (1) | CA2710523C (enExample) |
| CY (1) | CY1116076T1 (enExample) |
| DK (1) | DK2240477T3 (enExample) |
| ES (1) | ES2523695T3 (enExample) |
| HR (1) | HRP20141004T1 (enExample) |
| PL (1) | PL2240477T3 (enExample) |
| PT (1) | PT2240477E (enExample) |
| SI (1) | SI2240477T1 (enExample) |
| WO (1) | WO2009087419A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080051582A1 (en) | 2006-07-10 | 2008-02-28 | Sicor Inc. | Process for the preparation of tiotropium bromide |
| WO2011015884A1 (en) | 2009-08-07 | 2011-02-10 | Generics [Uk] Limited | Process to prepare scopine esters |
| CA2931876A1 (en) | 2009-08-07 | 2011-02-10 | Generics [Uk] Limited | Anhydrate of tiotropium bromide |
| WO2011095800A2 (en) | 2010-02-02 | 2011-08-11 | Generics [Uk] Limited | Analytical methods |
| TR201005221A2 (tr) * | 2010-04-01 | 2012-01-23 | Bi̇lgi̇ç Mahmut | Geliştirilmiş sentez metodu. |
| US8957209B2 (en) | 2010-04-01 | 2015-02-17 | Mahmut Bilgic | Methods for the synthesis of tiotropium bromide |
| TR201002520A2 (tr) * | 2010-04-01 | 2010-05-21 | Bi̇lgi̇ç Mahmut | Tiotropyum bromür imalat metodu. |
| TR201005222A2 (tr) * | 2010-04-01 | 2011-10-21 | Bi̇lgi̇ç Mahmut | Tiotropyum bromür sentez yöntemi |
| CN101979391B (zh) * | 2010-11-16 | 2013-06-05 | 济南德信佳生物科技有限公司 | 一种噻托溴铵的制备方法 |
| US8680297B2 (en) * | 2011-10-06 | 2014-03-25 | Drug Process Licensing Assoc., LLC | Manufacturing process for tiotropium bromide |
| PT106142B (pt) | 2012-02-10 | 2014-07-18 | Hovione Farmaci Ncia S A | Processo para a preparação de brometo de tiotrópio |
| CZ304808B6 (cs) | 2012-03-16 | 2014-11-05 | Zentiva, K.S. | Způsob přípravy skopinesteru kyseliny di(2-thienyl)glykolové, intermediátu v syntéze tiotropium bromidu a jeho nová forma |
| CZ305012B6 (cs) | 2012-03-30 | 2015-03-25 | Zentiva, K.S. | Způsob přípravy skopinesteru kyseliny di(2-thienyl)glykolové, intermediátu v syntéze tiotropium bromidu |
| WO2014140318A1 (en) * | 2013-03-14 | 2014-09-18 | K.H.S. Pharma Holding Gmbh | Improved process for acyl transfer reactions |
| CN117486893B (zh) * | 2023-12-29 | 2024-03-12 | 北京中医药大学深圳医院(龙岗) | anti-pso B及其在制备预防和/或治疗银屑病的药物中的应用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5610163A (en) * | 1989-09-16 | 1997-03-11 | Boehringer Ingelheim Gmbh | Esters of thienyl carboxylic acids and amino alcohols and their quaternization products |
| 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 |
| US6506900B1 (en) * | 2001-01-31 | 2003-01-14 | Boehringer Ingelheim Pharma Ag | Process for preparing a scopine ester intermediate |
| AUPR315301A0 (en) * | 2001-02-19 | 2001-03-15 | Silverbrook Research Pty. Ltd. | An Apparatus (ART102) |
| US6608055B2 (en) * | 2001-06-22 | 2003-08-19 | Boehringer Ingelheim Pharma Kg | Crystalline anticholinergic, processes for preparing it and its use for preparing a pharmaceutical composition |
| US6610849B2 (en) * | 2001-06-28 | 2003-08-26 | Boehringer Ingelheim Pharma Kg | Process for the manufacture of tropenol |
| DE10200943A1 (de) * | 2002-01-12 | 2003-07-24 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von Scopinestern |
| US6747153B2 (en) * | 2002-05-31 | 2004-06-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Industrial process for preparing tropenol |
| ATE435862T1 (de) * | 2003-05-28 | 2009-07-15 | Theravance Inc | Azabicycloalkanverbindungen als muscarinrezeptor antagonisten |
| US7968717B2 (en) * | 2003-11-03 | 2011-06-28 | Boehringer Ingelhein International Gmbh | Crystalline anhydrate with anticholinergic efficacy |
| JP5227790B2 (ja) * | 2005-05-02 | 2013-07-03 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規結晶性臭化チオトロピウム |
| DE102005035112A1 (de) * | 2005-07-27 | 2007-02-15 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neues Verfahren zur Herstellung von Tiotropiumsalzen unter Anwendung von in organischen Lösungsmitteln löslichen N-Methylscopiniumsalzen |
| US20070167480A1 (en) * | 2005-12-19 | 2007-07-19 | Sicor Inc. | Pure and stable tiotropium bromide |
| KR101395881B1 (ko) * | 2005-12-19 | 2014-05-21 | 시코르, 인크. | 브롬화 티오트로피움의 신규한 형태 및 이의 제조 방법 |
| US20080051582A1 (en) * | 2006-07-10 | 2008-02-28 | Sicor Inc. | Process for the preparation of tiotropium bromide |
| WO2008089852A1 (de) * | 2007-01-26 | 2008-07-31 | Boehringer Ingelheim Pharma Gmbh & Co.Kg | Neues verfahren zur herstellung von tiotropiumsalzen |
| WO2008104955A1 (en) * | 2007-02-28 | 2008-09-04 | Ranbaxy Laboratories Limited | Azoniatricyclo [3.3.1.0] nonane derivatives as muscarinic receptor antagonists |
-
2009
- 2009-01-09 HR HRP20141004AT patent/HRP20141004T1/hr unknown
- 2009-01-09 US US12/810,231 patent/US20110028508A1/en not_active Abandoned
- 2009-01-09 ES ES09701042.5T patent/ES2523695T3/es active Active
- 2009-01-09 PL PL09701042T patent/PL2240477T3/pl unknown
- 2009-01-09 JP JP2010541849A patent/JP6087492B2/ja not_active Expired - Fee Related
- 2009-01-09 WO PCT/GB2009/050014 patent/WO2009087419A1/en not_active Ceased
- 2009-01-09 CN CN201610056741.0A patent/CN105601628A/zh active Pending
- 2009-01-09 SI SI200931062T patent/SI2240477T1/sl unknown
- 2009-01-09 CA CA2710523A patent/CA2710523C/en not_active Expired - Fee Related
- 2009-01-09 DK DK09701042.5T patent/DK2240477T3/en active
- 2009-01-09 CN CN2009801017774A patent/CN101918401A/zh active Pending
- 2009-01-09 PT PT97010425T patent/PT2240477E/pt unknown
- 2009-01-09 EP EP09701042.5A patent/EP2240477B8/en active Active
- 2009-01-09 AU AU2009203579A patent/AU2009203579B2/en not_active Ceased
-
2014
- 2014-08-15 JP JP2014165472A patent/JP5902774B2/ja not_active Expired - Fee Related
- 2014-11-11 CY CY20141100937T patent/CY1116076T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009087419A1 (en) | 2009-07-16 |
| CY1116076T1 (el) | 2017-02-08 |
| CA2710523C (en) | 2014-11-18 |
| JP5902774B2 (ja) | 2016-04-13 |
| US20110028508A1 (en) | 2011-02-03 |
| AU2009203579B2 (en) | 2013-07-25 |
| JP2011509284A (ja) | 2011-03-24 |
| PL2240477T3 (pl) | 2015-03-31 |
| ES2523695T3 (es) | 2014-11-28 |
| CN101918401A (zh) | 2010-12-15 |
| PT2240477E (pt) | 2014-11-19 |
| AU2009203579A1 (en) | 2009-07-16 |
| HRP20141004T1 (hr) | 2015-02-13 |
| JP6087492B2 (ja) | 2017-03-01 |
| EP2240477B8 (en) | 2014-12-10 |
| EP2240477B1 (en) | 2014-09-10 |
| CA2710523A1 (en) | 2009-07-16 |
| EP2240477A1 (en) | 2010-10-20 |
| JP2014208718A (ja) | 2014-11-06 |
| SI2240477T1 (sl) | 2015-02-27 |
| DK2240477T3 (en) | 2014-12-08 |
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