USRE39820E1 - Esters of thienyl carboxylic acids and amino alcohols and their quaternization products - Google Patents
Esters of thienyl carboxylic acids and amino alcohols and their quaternization products Download PDFInfo
- Publication number
- USRE39820E1 USRE39820E1 US11/254,213 US25421305A USRE39820E US RE39820 E1 USRE39820 E1 US RE39820E1 US 25421305 A US25421305 A US 25421305A US RE39820 E USRE39820 E US RE39820E
- Authority
- US
- United States
- Prior art keywords
- thienyl
- tropanyl
- compound
- methobromide
- accordance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime, expires
Links
- 0 *OC(=O)C([1*])(C)O.C1=CSC=C1 Chemical compound *OC(=O)C([1*])(C)O.C1=CSC=C1 0.000 description 19
- GNMZHDNLEVWOJD-UHFFFAOYSA-N C.COC1CC2C=CC(C1)C2(C)C Chemical compound C.COC1CC2C=CC(C1)C2(C)C GNMZHDNLEVWOJD-UHFFFAOYSA-N 0.000 description 2
- QOHMEPDDHIKCRF-UHFFFAOYSA-N COC1CC2C3OC3C(C1)C2(C)C.[Br-] Chemical compound COC1CC2C3OC3C(C1)C2(C)C.[Br-] QOHMEPDDHIKCRF-UHFFFAOYSA-N 0.000 description 2
- RXCCRWNHSXHZEF-UHFFFAOYSA-N C.C.C.CC1OC1C.CC=CC.CCCC.CCCCC Chemical compound C.C.C.CC1OC1C.CC=CC.CCCC.CCCCC RXCCRWNHSXHZEF-UHFFFAOYSA-N 0.000 description 1
- XAPDXJZDEZJYAK-UHFFFAOYSA-N C.CC1CCCCC1 Chemical compound C.CC1CCCCC1 XAPDXJZDEZJYAK-UHFFFAOYSA-N 0.000 description 1
- MMSQWDLQGTVUKW-UHFFFAOYSA-N C.COC1CC2CCC(C1)C2(C)C(C)C Chemical compound C.COC1CC2CCC(C1)C2(C)C(C)C MMSQWDLQGTVUKW-UHFFFAOYSA-N 0.000 description 1
- JCDGIQLVQRDMDH-UHFFFAOYSA-N C.COC1CC2CCC(C1)C2(C)CCF Chemical compound C.COC1CC2CCC(C1)C2(C)CCF JCDGIQLVQRDMDH-UHFFFAOYSA-N 0.000 description 1
- KYDVGOMHXKTJMI-UHFFFAOYSA-N C.OC1CCCCC1 Chemical compound C.OC1CCCCC1 KYDVGOMHXKTJMI-UHFFFAOYSA-N 0.000 description 1
- ASUYNGITOVKEJM-UHFFFAOYSA-N C1=CSC=C1.CC(=O)C(C)(C1=CC=CS1)C1CCCCC1.CC(=O)C(C)C1=CC=CS1.CC(=O)C(O)(C1=CC=CC=C1)C1=CC=CS1.CC(=O)C(O)(C1=CC=CC=C1)C1=CSC=C1.CC(=O)C(O)(C1=CC=CO1)C1=CC=CS1.CC(=O)C(O)(C1=CC=CS1)C1=CC=CS1.CC(=O)C(O)(C1=CC=CS1)C1CCCC1.CC(=O)C(O)(C1=CC=CS1)C1CCCCC1.CC(=O)C(O)(C1=CSC=C1)C1=CSC=C1 Chemical compound C1=CSC=C1.CC(=O)C(C)(C1=CC=CS1)C1CCCCC1.CC(=O)C(C)C1=CC=CS1.CC(=O)C(O)(C1=CC=CC=C1)C1=CC=CS1.CC(=O)C(O)(C1=CC=CC=C1)C1=CSC=C1.CC(=O)C(O)(C1=CC=CO1)C1=CC=CS1.CC(=O)C(O)(C1=CC=CS1)C1=CC=CS1.CC(=O)C(O)(C1=CC=CS1)C1CCCC1.CC(=O)C(O)(C1=CC=CS1)C1CCCCC1.CC(=O)C(O)(C1=CSC=C1)C1=CSC=C1 ASUYNGITOVKEJM-UHFFFAOYSA-N 0.000 description 1
- NCCXZWAEQLVTCR-UHFFFAOYSA-N CC1(C)C2CC(OC(=O)C(O)(C3=CC=CC=C3)C3=CSC=C3)CC1C1OC12.[Br-] Chemical compound CC1(C)C2CC(OC(=O)C(O)(C3=CC=CC=C3)C3=CSC=C3)CC1C1OC12.[Br-] NCCXZWAEQLVTCR-UHFFFAOYSA-N 0.000 description 1
- ZTQCWRZJWGMGCH-UHFFFAOYSA-N CCCC1CC(CC)CC1 Chemical compound CCCC1CC(CC)CC1 ZTQCWRZJWGMGCH-UHFFFAOYSA-N 0.000 description 1
- YGWQBFPVFXEWEK-UHFFFAOYSA-N CN1(C)C2CC(OC(=O)C(O)(C3=CC=CS3)C3=CC=CS3)CC23C2C4OC42C31 Chemical compound CN1(C)C2CC(OC(=O)C(O)(C3=CC=CS3)C3=CC=CS3)CC23C2C4OC42C31 YGWQBFPVFXEWEK-UHFFFAOYSA-N 0.000 description 1
- HRAJPUASRLVMIE-UHFFFAOYSA-N CN1(C)C2CC=CC23CC(OC(=O)C(O)(C2=CC=CS2)C2=CC=CS2)CC31 Chemical compound CN1(C)C2CC=CC23CC(OC(=O)C(O)(C2=CC=CS2)C2=CC=CS2)CC31 HRAJPUASRLVMIE-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N [H]C1(C)OC1([H])C Chemical compound [H]C1(C)OC1([H])C PQXKWPLDPFFDJP-UHFFFAOYSA-N 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- 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
Definitions
- the invention relates to novel thienylcarboxylates of amino alcohols and their quaternary products and to the preparation of the novel compounds and their use as active ingredients in medicaments.
- R 1 preferably represents thienyl
- R 2 preferably represents OH
- the group —OA preferably has the ⁇ -configuration and is derived from, for example scopine, tropine, granatoline or 6,7-dehydrotropine or the corresponding nor-compounds; however, —OA may also have the ⁇ -configuration, as in pseudotropine, pseudoscopine.
- the substituent R is preferably a lower alkyl radical, such as CH 3 , C 2 H 5 , n-C 3 H 7 , i-C 3 H 7 , R′ is preferably CH 3 .
- R and R′ together are, for example —(CH 2 ) 5 —.
- halogen substituents for R F or, as second choice, Cl are suitable.
- R denotes a halogen-substituted or hydroxy-substituted alkyl radical, it is preferably —CH 2 —CH 2 F or —CH 2 —CH 2 OH.
- the group A represents, for example the radicals of scopine, N-ethylnorscopine, N-isopropylnorscopine, tropine, N-isopropylnortropine, 6,7-dehydrotropine, N- ⁇ -fluoroethylnortropine, N-isopropyl-6,7-dehydronortropine, N-methylgranatoline or the corresponding quaternary compounds, wherein the anion is preferably Br ⁇ or CH 3 SO 3 ⁇ .
- the quaternary compounds are particularly suitable for therapeutic application, whereas the tertiary compounds are important not only as active ingredients but also as intermediate products.
- the compounds of the invention are strong anti-cholinergic agents and have prolonged action. Action lasting at least 24 hours is achieved at inhaled dosages in the ⁇ g range. In addition, the toxicity is in the same range as the commercial product Ipratropium bromide, while at the same time the therapeutic effect is stronger.
- novel compounds are suitable, in accordance with their anti-cholinergic nature, for example for the treatment of chronic obstructive bronchitis and (slight to moderately severe) asthma, also for the treatment of vagally induced sinus bradycardia.
- the novel active ingredients in particular the quaternary compounds
- the application for sinus bradycardia is preferably carried out intravenously or orally. It has thus proved to be advantageous that the novel compounds leave the gastro/intestinal motility largely unaffected.
- the compounds of the invention are processed using known auxiliaries and/or excipients to give conventional galenic preparations, for example inhalation solutions, suspensions in liquified propellants, preparations containing liposomes or proliposomes, injection solutions, tablets, coated tablets, capsules, inhalation powders for use in conventional inhalation apparatus.
- conventional galenic preparations for example inhalation solutions, suspensions in liquified propellants, preparations containing liposomes or proliposomes, injection solutions, tablets, coated tablets, capsules, inhalation powders for use in conventional inhalation apparatus.
- Controlled dosage aerosol Active ingredient 0.005 Sorbitan trioleate 0.1 monofluorotrichloromethane and to 100 Difluorodichloromethane 2:3
- the suspension is poured into a conventional aerosol container with a dosage valve. 50 ⁇ l of suspension are preferably dispensed per actuation.
- the active ingredient may also be metered in a higher amount if required (for example 0.02 wt. %).
- Tablets Active ingredient according to the invention 0.05 Colloidal silicic acid 0.95 Lactose 65.00 Potato starch 28.00 Polyvinylpyrrolidone 3.00 Na cellulose glycolate 2.00 Magnesium stearate 1.00 The constituents are processed in conventional manner to give tablets of 200 mg.
- the advantageous properties of the novel compounds are shown, for example, in the inhibition of broncholysis in the rabbit (acetylcholine spasms intravenously).
- the maximum effect occurred after 10 to 40 minutes.
- the inhibiting effect had still not been reduced to half, that is to say the half effect time is more, in some cases considerably more, than 5 hours, as made clear by the residual effects after 5 hours listed below:
- R′′ represents a C 1 -C 4 -alkyl radical, preferably a methyl or ethyl radical (R 1 , R 2 and R a have the above meanings)
- R 1 , R 2 and R a have the above meanings
- R 1 , R 2 and R a have the above meanings
- Q′′ represents ⁇ NR or ⁇ NH and the OH group is in the ⁇ - or ⁇ -position, in the presence of a conventional transesterification catalyst, and the compound obtained is optionally quaternised
- the transesterification is carried out with heat in an organic solvent, for example toluene, xylene, heptane, or in a melt, strong bases such as sodium methylate, sodium ethylate, sodium hydride, metallic sodium, being used as catalyst. Reduced pressure is used to remove the released lower alcohol from the equilibrium, the alcohol is optionally distilled off azeotropically.
- the transesterification takes place at temperatures which in general do not exceed 95° C. Transesterification often proceeds more favourably in a melt.
- the free bases may be obtained in a manner known per se from acid addition salts of the tertiary amines using suitable basic compounds.
- Quaternisation is carried out in suitable solvents, for example acetonitrile or acetonitrile/methylene chloride, preferably at room temperature; a corresponding alkyl halide, for example alkyl bromide, is preferably used in the process as quaternising agent.
- suitable solvents for example acetonitrile or acetonitrile/methylene chloride, preferably at room temperature; a corresponding alkyl halide, for example alkyl bromide, is preferably used in the process as quaternising agent.
- Transesterification products wherein Q′ represents NH are used as starting materials for those compounds in which R and R′ together represent a C 4 -C 6 -alkylene group. Conversion into the tertiary and then quaternary compound then takes place with the aid of suitable 1,4-dihaloalkanes, 1,5-dihaloalkanes or 1,6-dihaloalkanes without isolation of intermediates.
- the starting materials may be obtained analogously to known compounds—in as much as they have not already been described.
- Pseudoscopine may be obtained in accordance with M. Polonovski et al., Bull. soc. chim. 43, 79 (1928). Pseudotropenol may be removed from the mixture, (fractional crystallisation or distillation) which is obtained, for example in accordance with V. Hayakawa et al., J. Amer. Chem. Soc. 1978, 100(6), 1786 or R. Noyori et al., J. Amer. Chem. Soc. 1974, 96(10), 3336.
- the corresponding methyl esters may be prepared in a conventional manner starting from 2-furylglyoxylnitrile or 3-furylglyoxylnitrile via the 2-furylglyoxylic acid or 3-furylglyoxylic acid which can be obtained therefrom.
- the corresponding glycolates are obtained from these as described using the organometallic derivatives of 2-bromothiophene or 3-bromothiophene.
- the organometallic compounds which can be obtained from 2-, 3- or 4-halopyridine can be reacted with methyl 2-thienylglyoxylate or methyl 3-thienylglyoxylate to give the corresponding glycolates.
- Thienylglycolates in which the thiophene ring contains fluorine in the 2- or 3-position, are prepared, for example starting from 2-fluorothiophene or 3-fluorothiophene (bromination to give 2-bromo-3-fluorothiophene or 2-bromo-5-fluorothiophene), and after conversion to the corresponding organometallic compounds, reaction with suitable glyoxylates to give the glycolates.
- 2-Fluorothiophene and 3-fluorothiophene can be reacted analogously to give the corresponding glyoxylates Unterhalt, Arch. Pharm. 322, 839 (1989) which in turn, as already described, may be reacted with, for example 2-thienyl or 3-thienyl derivatives, to give glycolates.
- Symmetrically substituted di-thienylglycolates can be prepared analogously by selecting suitable components.
- a further route is available via a process analogous to the benzoin condensation and benzilic acid rearrangement.
- the scopine di-(2-thienyl)glycolate is extracted from the combined aqueous phases using methylene chloride after adding the corresponding amount of sodium carbonate and dried over sodium sulphate.
- the hydrochloride is prepared from the dried methylene chloride solution in a conventional manner. The crystals are filtered off under suction, washed using acetone and dried under reduced pressure at 35° C. Pale yellow crystals (from methanol), m.p. 238°-41° C. (decomposition);
- the hydrochloride may be converted to the base in a conventional manner.
- the hydrochloride of the basic ester crystallising out is filtered off under suction and washed using a small amount of water and a large amount of diethyl ether.
- the filtrate phases are separated off and the aqueous phase is extracted using diethyl ether.
- the hydrochloride filtered off under suction is suspended in the (acid) aqueous phase and converted to the base while monitoring the temperature and adding the corresponding amount of sodium carbonate; the base is extracted using methylene chloride.
- the combined methylene chloride phases are dried over sodium sulphate. After distilling off the methylene chloride, crystals remain which are purified over active charcoal and recrystallised from acetonitrile. Pale yellow crystals (from acetonitrile), m.p. 148°-49° C.;
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Glass Compositions (AREA)
- Compositions Of Oxide Ceramics (AREA)
- Disintegrating Or Milling (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/254,213 USRE39820E1 (en) | 1989-09-16 | 2005-10-18 | Esters of thienyl carboxylic acids and amino alcohols and their quaternization products |
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3931041A DE3931041C2 (de) | 1989-09-16 | 1989-09-16 | Ester von Thienylcarbonsäuren mit Aminoalkoholen, ihre Quaternierungsprodukte, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
DE3931041.8 | 1989-09-16 | ||
EPPCT/EP90/01517 | 1990-09-08 | ||
PCT/EP1990/001517 WO1991004252A1 (de) | 1989-09-16 | 1990-09-08 | Neue thienylcarbonsäureester von aminoalkoholen, ihre quaternierungsprodukte sowie die herstellung und verwendung dieser verbindungen |
US83872492A | 1992-03-13 | 1992-03-13 | |
US10082293A | 1993-08-02 | 1993-08-02 | |
US25432494A | 1994-06-06 | 1994-06-06 | |
US08/405,111 US5610163A (en) | 1989-09-16 | 1995-03-16 | Esters of thienyl carboxylic acids and amino alcohols and their quaternization products |
US11/254,213 USRE39820E1 (en) | 1989-09-16 | 2005-10-18 | Esters of thienyl carboxylic acids and amino alcohols and their quaternization products |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/405,111 Reissue US5610163A (en) | 1989-09-16 | 1995-03-16 | Esters of thienyl carboxylic acids and amino alcohols and their quaternization products |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE39820E1 true USRE39820E1 (en) | 2007-09-04 |
Family
ID=6389619
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/254,213 Expired - Lifetime USRE39820E1 (en) | 1989-09-16 | 2005-10-18 | Esters of thienyl carboxylic acids and amino alcohols and their quaternization products |
Country Status (33)
Country | Link |
---|---|
US (1) | USRE39820E1 (uk) |
EP (1) | EP0418716B1 (uk) |
JP (1) | JPH0730074B2 (uk) |
KR (1) | KR0168432B1 (uk) |
AT (1) | ATE103914T1 (uk) |
AU (1) | AU642913B2 (uk) |
BG (1) | BG61295B2 (uk) |
CA (1) | CA2066248C (uk) |
CZ (1) | CZ284589B6 (uk) |
DD (1) | DD297647A5 (uk) |
DE (3) | DE3931041C2 (uk) |
DK (1) | DK0418716T3 (uk) |
ES (1) | ES2052125T3 (uk) |
FI (1) | FI114395B (uk) |
HR (1) | HRP940723B1 (uk) |
HU (2) | HU208823B (uk) |
IE (1) | IE65528B1 (uk) |
IL (1) | IL95691A (uk) |
LU (1) | LU90949I2 (uk) |
MX (1) | MX9203150A (uk) |
NL (1) | NL300084I2 (uk) |
NO (2) | NO301478B1 (uk) |
NZ (1) | NZ235306A (uk) |
PH (1) | PH31617A (uk) |
PL (1) | PL168468B1 (uk) |
PT (1) | PT95312B (uk) |
RU (1) | RU2073677C1 (uk) |
SI (1) | SI9011744B (uk) |
SK (1) | SK279453B6 (uk) |
UA (1) | UA41272C2 (uk) |
WO (1) | WO1991004252A1 (uk) |
YU (1) | YU47800B (uk) |
ZA (1) | ZA907338B (uk) |
Cited By (33)
Publication number | Priority date | Publication date | Assignee | Title |
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US20050143410A1 (en) * | 2003-11-03 | 2005-06-30 | Boehringer Ingelheim International Gmbh | Novel crystalline anhydrate with anticholinergic efficacy |
US20060154951A1 (en) * | 2003-01-16 | 2006-07-13 | Wood Ronald W | Quaternary antimuscarinic compounds for the treatment of bladder diseases |
US20070015785A1 (en) * | 2002-03-20 | 2007-01-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Crystalline Micronisate, Process for the Manufacture Thereof and Use Thereof for the Preparation of a Medicament |
US20070155773A1 (en) * | 2006-01-04 | 2007-07-05 | Michael Engel | Use of Tiotropium Salts in the Treatment of Moderate Persistent Asthma |
US20090134655A1 (en) * | 2007-10-29 | 2009-05-28 | Carl Paluszkiewicz | Motorcycle wind deflector accessory support |
US20090299042A1 (en) * | 2006-07-21 | 2009-12-03 | Nuria Busquets Baque | Process for manufacturing 3(r)-(2-hydroxy-2,2-dithien-2-ylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide |
WO2010101538A2 (en) | 2009-03-06 | 2010-09-10 | Bilgic Mahmut | New crystal forms |
WO2010138868A2 (en) | 2009-05-29 | 2010-12-02 | Pearl Therapeutics, Inc. | Compositions for pulmonary delivery of long-acting muscarinic antagonists and long-acting b2 adrenergic receptor agonists and associated methods and systems |
US20110020454A1 (en) * | 2008-03-13 | 2011-01-27 | Rosa Lamarca Casado | Novel dosage and formulation |
US8088127B2 (en) | 2008-05-09 | 2012-01-03 | Innovative Pulmonary Solutions, Inc. | Systems, assemblies, and methods for treating a bronchial tree |
US8172827B2 (en) | 2003-05-13 | 2012-05-08 | Innovative Pulmonary Solutions, Inc. | Apparatus for treating asthma using neurotoxin |
US8324266B2 (en) | 2009-05-29 | 2012-12-04 | Pearl Therapeutics, Inc. | Compositions, methods and systems for respiratory delivery of two or more active agents |
US20130030182A1 (en) * | 2010-04-01 | 2013-01-31 | Mahmut Bilgic | Methods for the synthesis of tiotropium bromide |
US8483831B1 (en) | 2008-02-15 | 2013-07-09 | Holaira, Inc. | System and method for bronchial dilation |
US8513279B2 (en) | 1999-07-14 | 2013-08-20 | Almirall, S.A. | Quinuclidine derivatives and medicinal compositions containing the same |
US8680297B2 (en) | 2011-10-06 | 2014-03-25 | Drug Process Licensing Assoc., LLC | Manufacturing process for tiotropium bromide |
US8740895B2 (en) | 2009-10-27 | 2014-06-03 | Holaira, Inc. | Delivery devices with coolable energy emitting assemblies |
WO2014165303A1 (en) | 2013-04-01 | 2014-10-09 | Pulmatrix, Inc. | Tiotropium dry powders |
US8911439B2 (en) | 2009-11-11 | 2014-12-16 | Holaira, Inc. | Non-invasive and minimally invasive denervation methods and systems for performing the same |
US9149328B2 (en) | 2009-11-11 | 2015-10-06 | Holaira, Inc. | Systems, apparatuses, and methods for treating tissue and controlling stenosis |
US9398933B2 (en) | 2012-12-27 | 2016-07-26 | Holaira, Inc. | Methods for improving drug efficacy including a combination of drug administration and nerve modulation |
WO2016185282A1 (en) | 2015-05-18 | 2016-11-24 | Glenmark Specialty S.A. | Tiotropium inhalation solution for nebulization |
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- 1992-03-13 NO NO921002A patent/NO301478B1/no not_active IP Right Cessation
- 1992-03-13 IE IE334290A patent/IE65528B1/en active Protection Beyond IP Right Term
- 1992-03-13 FI FI921087A patent/FI114395B/fi active Protection Beyond IP Right Term
- 1992-03-13 PL PL90286900A patent/PL168468B1/pl active Protection Beyond IP Right Term
- 1992-06-23 MX MX9203150A patent/MX9203150A/es unknown
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1994
- 1994-02-23 BG BG98532A patent/BG61295B2/bg unknown
- 1994-10-21 HR HRP-1744/90A patent/HRP940723B1/xx not_active IP Right Cessation
- 1994-12-15 HU HU94P/P00055P patent/HU210612A9/hu unknown
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2002
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- 2002-08-30 LU LU90949C patent/LU90949I2/fr unknown
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2005
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