UA82909C2 - Novel crystalline anhydride with anticholinergic effect - Google Patents

Novel crystalline anhydride with anticholinergic effect Download PDF

Info

Publication number: UA82909C2
Authority: UA; Ukraine
Prior art keywords: tiotropium bromide; proposed; inhalation; medicinal product; cyclodextrin
Prior art date: 2003-11-03

Application number

UAA200605766A

Other languages

English (en)

Ukrainian (uk)

Inventor

Waldemar Pfrengle

Peter Sieger

Original Assignee

Boehringer Ingelheim Int

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.)

2003-11-03

Filing date

2004-10-29

Publication date

2008-05-26

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34530662&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=UA82909(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2004-10-29 Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int

2008-05-26 Publication of UA82909C2 publication Critical patent/UA82909C2/uk

Links

150000008064 anhydrides Chemical class 0.000 title abstract 3
230000001078 anti-cholinergic effect Effects 0.000 title 1
229960000257 tiotropium bromide Drugs 0.000 claims abstract description 53
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 51
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 9
208000006673 asthma Diseases 0.000 claims abstract description 9
208000018569 Respiratory Tract disease Diseases 0.000 claims abstract description 8
239000003814 drug Substances 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 59
239000000843 powder Substances 0.000 claims description 56
239000000725 suspension Substances 0.000 claims description 34
239000000126 substance Substances 0.000 claims description 25
239000003380 propellant Substances 0.000 claims description 22
229940126601 medicinal product Drugs 0.000 claims description 16
239000000443 aerosol Substances 0.000 claims description 13
-1 polysaccharides alcohols Chemical class 0.000 claims description 13
239000000546 pharmaceutical excipient Substances 0.000 claims description 12
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 12
238000002360 preparation method Methods 0.000 claims description 11
229940110309 tiotropium Drugs 0.000 claims description 10
229920000858 Cyclodextrin Polymers 0.000 claims description 9
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 claims description 9
239000008101 lactose Substances 0.000 claims description 9
238000005507 spraying Methods 0.000 claims description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
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 claims description 3
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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 claims description 3
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ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
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150000001413 amino acids Chemical class 0.000 claims description 2
PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 2
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 2
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HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims 1
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239000000600 sorbitol Substances 0.000 claims 1
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HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims 1
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238000004519 manufacturing process Methods 0.000 abstract description 3
239000002775 capsule Substances 0.000 description 31
239000013543 active substance Substances 0.000 description 27
238000000034 method Methods 0.000 description 25
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
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PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
230000000181 anti-adherent effect Effects 0.000 description 1
229960003237 betaine Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229960000846 camphor Drugs 0.000 description 1
229930008380 camphor Natural products 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
229960001927 cetylpyridinium chloride Drugs 0.000 description 1
NFCRBQADEGXVDL-UHFFFAOYSA-M cetylpyridinium chloride monohydrate Chemical compound O.[Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NFCRBQADEGXVDL-UHFFFAOYSA-M 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
235000017803 cinnamon Nutrition 0.000 description 1
229960004106 citric acid Drugs 0.000 description 1
239000011362 coarse particle Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
238000002050 diffraction method Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229940068939 glyceryl monolaurate Drugs 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
229920001903 high density polyethylene Polymers 0.000 description 1
239000004700 high-density polyethylene Substances 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
229940041616 menthol Drugs 0.000 description 1
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
238000012856 packing Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 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
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
238000007790 scraping Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
229940037001 sodium edetate Drugs 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
229940012831 stearyl alcohol Drugs 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
229940117972 triolein Drugs 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 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)
Medicinal Preparation (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

UAA200605766A 2003-11-03 2004-10-29 Novel crystalline anhydride with anticholinergic effect UA82909C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP03025077		2003-11-03
PCT/EP2004/012269 WO2005042527A1 (fr)	2003-11-03	2004-10-29	Nouvel anhydrate cristallin a effet anticholinergique

Publications (1)

Publication Number	Publication Date
UA82909C2 true UA82909C2 (en)	2008-05-26

Family

ID=34530662

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200605766A UA82909C2 (en)	2003-11-03	2004-10-29	Novel crystalline anhydride with anticholinergic effect

Country Status (33)

Country	Link
EP (1)	EP1682542B1 (fr)
JP (1)	JP4553902B2 (fr)
KR (2)	KR101313904B1 (fr)
CN (1)	CN100509809C (fr)
AR (1)	AR046319A1 (fr)
AT (1)	ATE453641T1 (fr)
AU (1)	AU2004285684B2 (fr)
BR (1)	BRPI0415636A (fr)
CA (1)	CA2544352C (fr)
CO (1)	CO5690641A2 (fr)
CY (1)	CY1110339T1 (fr)
DE (1)	DE502004010602D1 (fr)
DK (1)	DK1682542T3 (fr)
EA (1)	EA008587B1 (fr)
EC (1)	ECSP066543A (fr)
ES (1)	ES2338563T3 (fr)
HR (1)	HRP20100029T1 (fr)
IL (1)	IL175126A (fr)
ME (1)	ME00349B (fr)
MX (1)	MX272045B (fr)
MY (1)	MY146628A (fr)
NO (1)	NO20062569L (fr)
NZ (1)	NZ547581A (fr)
PE (1)	PE20050996A1 (fr)
PL (1)	PL1682542T3 (fr)
PT (1)	PT1682542E (fr)
RS (2)	RS51599B (fr)
SI (1)	SI1682542T1 (fr)
TW (1)	TWI336330B (fr)
UA (1)	UA82909C2 (fr)
UY (1)	UY28596A1 (fr)
WO (1)	WO2005042527A1 (fr)
ZA (1)	ZA200602344B (fr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1879888A2 (fr) *	2005-05-02	2008-01-23	Boehringer Ingelheim International GmbH	Formes cristallines de bromure de tiotropium
RU2453547C2 (ru) *	2005-12-19	2012-06-20	Сикор Инк.	Новые формы тиотропия бромида и способы их получения
US9108962B2 (en)	2005-12-19	2015-08-18	Sicor, Inc.	Forms of tiotropium bromide and processes for preparation thereof
PT1869035E (pt) *	2005-12-19	2013-01-10	Sicor Inc	Novas formas de brometo de tiotrópio e processos para sua preparação
KR20080083060A (ko) *	2006-01-04	2008-09-12	베링거 인겔하임 인터내셔날 게엠베하	중등 지속성 천식의 치료에서 티오트로퓸 염의 용도
CN100999521B (zh) *	2006-01-13	2010-12-08	江苏正大天晴药业股份有限公司	结晶性抗胆碱药噻托溴铵
US20080051582A1 (en)	2006-07-10	2008-02-28	Sicor Inc.	Process for the preparation of tiotropium bromide
CN101032484B (zh) *	2007-04-02	2010-05-26	南京卡文迪许生物工程技术有限公司	一种噻托溴铵胶囊型吸入粉雾剂
GB0716026D0 (en)	2007-08-16	2007-09-26	Norton Healthcare Ltd	An inhalable medicament
BRPI0916047A2 (pt) *	2008-11-04	2015-11-10	Cipla Ltd	composição farmacêutica em aerossol, uso de uma composição farmacêutica em aerossol, método para tratamento de sintomas crônicos ou agudos severos, moderados ou leves, ou para tratamento profilático de um distúrbio respiratório, dispensador farmacêutico em aerossol, processo para fabricação de um dispensador farmacêutico em aerossol e processo para fabricação de um complexo de um agente ativo e um adjuvante
AU2009312582B2 (en) *	2008-11-04	2014-03-27	Cipla Limited	Tiotropium bromide having a low degree of crystallinity
CA2768553C (fr)	2009-08-07	2016-08-02	Generics [Uk] Limited	Anhydrate de bromure de tiotropium
TR201111589A2 (tr) *	2011-03-03	2012-09-21	Bi̇lgi̇ç Mahmut	Tiotropyum bromür susuz kristal formu.
CZ304368B6 (cs)	2011-11-28	2014-04-02	Zentiva, K.S.	Směsný solvát tiotropium bromidu a způsob jeho přípravy
GB201200525D0 (en)	2011-12-19	2012-02-29	Teva Branded Pharmaceutical Prod R & D Inc	An inhalable medicament
EP2897955B1 (fr) *	2012-09-11	2019-11-06	Bilgic, Mahmut	Nouvelle forme cristalline du bromure de tiotropium
ES2620758T3 (es)	2012-11-05	2017-06-29	Zentiva K.S.	Estabilización de solvatos de tiotropio
EP2913332A1 (fr)	2014-02-27	2015-09-02	Euticals S.P.A.	Forme cristalline de bromure de tiotropium et de lactose
US10034866B2 (en)	2014-06-19	2018-07-31	Teva Branded Pharmaceutical Products R&D, Inc.	Inhalable medicament comprising tiotropium
WO2017138896A1 (fr)	2016-02-11	2017-08-17	Sima Patent Ve Lisanslama Hizmetleri Ltd. Şti	Forme cristalline d'anhydrate de bromure de tiotropium
EP4108230A1 (fr)	2021-06-24	2022-12-28	Laboratoires SMB	Nouvelle composition de poudre sèche de tiotropium pour inhalation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
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
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
DE10111843A1 (de) *	2001-03-13	2002-09-19	Boehringer Ingelheim Pharma	Verbindungen zur Behandlung von inflammatorischen Erkrankungen
CA2450961C (fr) *	2001-06-22	2010-03-30	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Substance anticholinergique cristalline, procedes de production et son utilisation pour la production de composition pharmaceutique

2004
- 2004-10-29 WO PCT/EP2004/012269 patent/WO2005042527A1/fr not_active Ceased
- 2004-10-29 DE DE502004010602T patent/DE502004010602D1/de not_active Expired - Lifetime
- 2004-10-29 ES ES04791029T patent/ES2338563T3/es not_active Expired - Lifetime
- 2004-10-29 KR KR1020127007695A patent/KR101313904B1/ko not_active Expired - Fee Related
- 2004-10-29 PT PT04791029T patent/PT1682542E/pt unknown
- 2004-10-29 UA UAA200605766A patent/UA82909C2/uk unknown
- 2004-10-29 RS RS20060291A patent/RS51599B/sr unknown
- 2004-10-29 CN CNB200480032521XA patent/CN100509809C/zh not_active Expired - Lifetime
- 2004-10-29 CA CA2544352A patent/CA2544352C/fr not_active Expired - Fee Related
- 2004-10-29 EP EP04791029A patent/EP1682542B1/fr not_active Expired - Lifetime
- 2004-10-29 AU AU2004285684A patent/AU2004285684B2/en not_active Ceased
- 2004-10-29 JP JP2006537208A patent/JP4553902B2/ja not_active Expired - Lifetime
- 2004-10-29 BR BRPI0415636-6A patent/BRPI0415636A/pt not_active IP Right Cessation
- 2004-10-29 KR KR1020067010918A patent/KR101285571B1/ko not_active Expired - Fee Related
- 2004-10-29 ME MEP-2008-517A patent/ME00349B/fr unknown
- 2004-10-29 EA EA200600853A patent/EA008587B1/ru unknown
- 2004-10-29 AT AT04791029T patent/ATE453641T1/de active
- 2004-10-29 RS YUP-2006/0291A patent/RS20060291A/sr unknown
- 2004-10-29 PE PE2004001047A patent/PE20050996A1/es active IP Right Grant
- 2004-10-29 PL PL04791029T patent/PL1682542T3/pl unknown
- 2004-10-29 DK DK04791029.4T patent/DK1682542T3/da active
- 2004-10-29 SI SI200431356T patent/SI1682542T1/sl unknown
- 2004-10-29 NZ NZ547581A patent/NZ547581A/en not_active IP Right Cessation
- 2004-10-29 HR HR20100029T patent/HRP20100029T1/hr unknown
- 2004-11-01 MY MYPI20044518A patent/MY146628A/en unknown
- 2004-11-02 TW TW093133282A patent/TWI336330B/zh not_active IP Right Cessation
- 2004-11-03 UY UY28596A patent/UY28596A1/es not_active Application Discontinuation
- 2004-11-03 AR ARP040104040A patent/AR046319A1/es unknown
2006
- 2006-03-22 ZA ZA200602344A patent/ZA200602344B/en unknown
- 2006-04-24 IL IL175126A patent/IL175126A/en active IP Right Grant
- 2006-05-02 CO CO06041173A patent/CO5690641A2/es not_active Application Discontinuation
- 2006-05-03 EC EC2006006543A patent/ECSP066543A/es unknown
- 2006-05-03 MX MXPA06004940 patent/MX272045B/es active IP Right Grant
- 2006-06-02 NO NO20062569A patent/NO20062569L/no not_active Application Discontinuation
2010
- 2010-02-09 CY CY20101100120T patent/CY1110339T1/el unknown

Also Published As

Publication number	Publication date
MX272045B (en)	2009-11-23
IL175126A0 (en)	2006-09-05
TW200526652A (en)	2005-08-16
ZA200602344B (en)	2007-07-25
KR101313904B1 (ko)	2013-09-30
CY1110339T1 (el)	2015-01-14
WO2005042527A1 (fr)	2005-05-12
KR101285571B1 (ko)	2013-07-15
NZ547581A (en)	2009-03-31
ME00349B (fr)	2011-05-10
RS20060291A (sr)	2008-06-05
CN100509809C (zh)	2009-07-08
PT1682542E (pt)	2010-01-27
EP1682542A1 (fr)	2006-07-26
EA200600853A1 (ru)	2006-10-27
CN1875019A (zh)	2006-12-06
HRP20100029T1 (hr)	2010-02-28
JP4553902B2 (ja)	2010-09-29
AR046319A1 (es)	2005-11-30
PE20050996A1 (es)	2005-12-20
AU2004285684A1 (en)	2005-05-12
CO5690641A2 (es)	2006-10-31
MEP51708A (en)	2011-02-10
TWI336330B (en)	2011-01-21
SI1682542T1 (sl)	2010-04-30
DE502004010602D1 (de)	2010-02-11
MXPA06004940A (es)	2006-07-20
EP1682542B1 (fr)	2009-12-30
AU2004285684B2 (en)	2011-07-14
ATE453641T1 (de)	2010-01-15
JP2007509894A (ja)	2007-04-19
PL1682542T3 (pl)	2010-06-30
RS51599B (sr)	2011-08-31
EA008587B1 (ru)	2007-06-29
IL175126A (en)	2010-11-30
HK1099752A1 (zh)	2007-08-24
KR20120036381A (ko)	2012-04-17
NO20062569L (no)	2006-07-12
CA2544352A1 (fr)	2005-05-12
BRPI0415636A (pt)	2006-12-12
CA2544352C (fr)	2013-07-16
UY28596A1 (es)	2005-06-30
KR20060121131A (ko)	2006-11-28
MY146628A (en)	2012-09-14
ECSP066543A (es)	2006-10-17
DK1682542T3 (da)	2010-05-10
ES2338563T3 (es)	2010-05-10

Publication	Publication Date	Title
RU2417224C2 (ru)	2011-04-27	Новые кристаллические формы тиотропийбромида
EA008587B1 (ru)	2007-06-29	Новый кристаллический ангидрат с антихолинергическим действием
AU2008203057B2 (en)	2011-12-08	Inhalation capsules
US20090137621A1 (en)	2009-05-28	Capsules Containing Inhalable Tiotropium
MX2007013691A (es)	2008-01-21	Nuevas formas cristalinas de bromuro de tiotropio.
EA010588B1 (ru)	2008-10-30	Порошковые лекарственные средства, содержащие соль тиотропия и ксинафоат салметерола
US7968717B2 (en)	2011-06-28	Crystalline anhydrate with anticholinergic efficacy
UA82414C2 (uk)	2008-04-10	Солі тіотропію, спосіб їх одержання, а також лікарські композиції, які їх містять
UA82413C2 (uk)	2008-04-10	Спосіб одержання солей тіотропію, солі тіотропію, а також лікарський засіб, який їх містить
EA007239B1 (ru)	2006-08-25	Суспензионные препараты с пропеллентом hfa, содержащие антихолинергическое средство
HK1099752B (en)	2009-11-27	Novel crystalline anhydrate with anticholinergic effect
HK1114856B (en)	2012-03-02	Novel crystalline forms of tiotropium bromide