WO1997012614A1 - Administration by inhalation of 2-amino-6n-propylamino-4,5,6,7-tetrahydrobenzothiazol, in particular of its (-)enantiomer and its pharmacologically tolerable acid addition salts - Google Patents
Administration by inhalation of 2-amino-6n-propylamino-4,5,6,7-tetrahydrobenzothiazol, in particular of its (-)enantiomer and its pharmacologically tolerable acid addition salts Download PDFInfo
- Publication number
- WO1997012614A1 WO1997012614A1 PCT/EP1996/004327 EP9604327W WO9712614A1 WO 1997012614 A1 WO1997012614 A1 WO 1997012614A1 EP 9604327 W EP9604327 W EP 9604327W WO 9712614 A1 WO9712614 A1 WO 9712614A1
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- WIPO (PCT)
- Prior art keywords
- amino
- acid addition
- propyl
- treatment
- inhalation
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 11
- 150000003839 salts Chemical class 0.000 title claims description 11
- FASDKYOPVNHBLU-UHFFFAOYSA-N N6-Propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine Chemical compound C1C(NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-UHFFFAOYSA-N 0.000 title description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- KWFASKPXXSVNIQ-UHFFFAOYSA-N 6-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,4-diamine Chemical compound C1C(CCC)CC(N)C2=C1SC(N)=N2 KWFASKPXXSVNIQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002831 pharmacologic agent Substances 0.000 claims 2
- 208000027898 Parkinson disease 7 Diseases 0.000 claims 1
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 9
- 229960003089 pramipexole Drugs 0.000 description 7
- 239000000443 aerosol Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000036765 blood level Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229940041682 inhalant solution Drugs 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 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 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000037058 blood plasma level Effects 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 238000009101 premedication Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960000257 tiotropium bromide Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229940072690 valium Drugs 0.000 description 1
Classifications
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
Definitions
- the present invention relates to the inhalation application of 2-amino-6n-propylamino-4,5,6,7-tetrahydrobenzothiazole, in particular its (-) - enantiomer, and its pharmacologically acceptable acid addition salts.
- Parkinson's disease is usually treated by oral administration of drugs.
- the inhalative application proposed according to the invention brings with it significant advantages for Parkinson's patients which improve their living conditions. Parkinson's disease is associated with a state of sedation in many patients.
- the inhalation application of Pramipexole according to the invention leads to an exceptionally rapid rise in blood level values within a very short time (minutes), as a result of which the state of the inhibition of movement is quickly eliminated. When administered orally, it can take up to two hours until optimal blood levels are reached.
- 2-Amino-6n-propyl-amino-4,5,6,7-tetrahydrobenzothiazole can be used in the form of its acid addition salts in the form of aqueous or ethanolic solutions for the preparation of an aerosol for use in accordance with the invention.
- the preferred acid addition salt is dihydrochloride.
- Devices for generating a metered dose aerosol are known from the prior art for the treatment of asthma diseases.
- a device as described in WO 91/14468 - Atomization Devices and Methods - is particularly preferred. is disclosed.
- the advantage of the device described there is that the propellant gases usually required for metered dose mhaiers (MDI's) for producing the aerosol can be dispensed with
- pramipexole can also be applied using a so-called powder inhaler, in which micronized particles in a range from 1 to 15, preferably 4 to 8, ⁇ m of the active ingredient are inhaled directly as a powder.
- Nembutal 30 mg / kg IV
- the active ingredient was administered by means of Respimat blood plasma level: inhalation 2 mg
- the buffer substances, the active substance and sodium pyrosulfite are successively dissolved in boiled water and cooled with CO 2 gassing. Make up to the given volume with boiled water and filter without pyrogen.
- the inhalation solution must be prepared and filled in darkened rooms.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The administration by inhalation of pramipexols is disclosed.
Description
Inhalative Applikation von 2-Amino-6n-propyl-amino-4.5.6.7-tetrahvdrobenzothiazol insbesondere seines (-)-Enantiomeren. sowie deren pnarmakoloqisch verträgliche SäureadditionssalzeInhalative administration of 2-amino-6n-propyl-amino-4.5.6.7-tetrahvdrobenzothiazole, especially its (-) - enantiomer. as well as their pharmacologically compatible acid addition salts
Die vorliegende Erfindung betrifft die inhalative Applikation von 2-Amino-6n-propyl- amino-4,5,6,7-tetrahydrobenzothιazol, insbesondere seines (-)-Enantiomeren, sowie deren pharmakologisch verträgliche Säureadditionssalze.The present invention relates to the inhalation application of 2-amino-6n-propylamino-4,5,6,7-tetrahydrobenzothiazole, in particular its (-) - enantiomer, and its pharmacologically acceptable acid addition salts.
Die genannten Verbindungen sind als Arzneimittel bekannt, wobei die Behandlung der Schizophrenie und die Behandlung der Parkmsonschen Krankheit im Vordergrund stehen. Einzelheiten zur Herstellung dieser Verbindungen - deren (-)- Enantiomeren in der Literatur auch als SND 919 oder Pramipexol bezeichnet wird, können der Europäischen Patentanmeldung EP-A 85 116 016 entnommen werden Aus dem europäischen Patent 428 038 ist die transdermale Applikation dieser Verbindung bekannt. Überraschenderweise hat sich gezeigt, daß Pramipexol in Form einer inhalativen Gabe besonders vorteilhaft appliziert werden kann, da ein schneller Wirkungseintritt bei gleichzeitig guter Verträglichkeit beobachtet wird.The compounds mentioned are known as medicaments, the treatment of schizophrenia and the treatment of Parkmson's disease being in the foreground. Details of the preparation of these compounds - whose (-) - enantiomers are also referred to in the literature as SND 919 or pramipexole can be found in European patent application EP-A 85 116 016. European patent 428 038 discloses the transdermal application of this compound. Surprisingly, it has been shown that pramipexole can be administered particularly advantageously in the form of an inhalation, since a rapid onset of action with good tolerability is observed.
Die Behandlung der Parkinsonschen Krankheit erfolgt üblicherweise durch orale Applikation von Arzneimitteln. Die erfindungsgemäß vorgeschlagene inhalative Applikation bringt für den Parkinson-Patienten wesentliche Vorteile mit sich, die seine Lebensumstände verbessern. Die Parkinson'sche Erkrankung ist bei vielen Patienten mit einem Zustand der Bewegungshemmung verbunden. Die erfindungsgemäße inhalative Applikation von Pramipexole führt zu einem außergewöhnlich raschem Anstieg der Blutspiegelwerte innerhalb kürzester Zeit (Minuten) wodurch der Zustand der Bewegungshemmung rasch aufgehoben wird. Bei oraler Applikation kann es bis zu zwei Stunden dauern, bis optimale Blutspiegelwerte erreicht sind.Parkinson's disease is usually treated by oral administration of drugs. The inhalative application proposed according to the invention brings with it significant advantages for Parkinson's patients which improve their living conditions. Parkinson's disease is associated with a state of sedation in many patients. The inhalation application of Pramipexole according to the invention leads to an exceptionally rapid rise in blood level values within a very short time (minutes), as a result of which the state of the inhibition of movement is quickly eliminated. When administered orally, it can take up to two hours until optimal blood levels are reached.
2-Amino-6n-propyl-amino-4,5,6,7-tetrahydrobenzothiazol kann in Form seiner Säureadditionssalze in Form von wässerigen oder ethanolischen Lösungen zur Herstellung eines Aerosols zur erfindungsgemäßen Anwendung verwendet werden. Bevorzugtes Säureadditionssalz ist das Dihydrochlorid.2-Amino-6n-propyl-amino-4,5,6,7-tetrahydrobenzothiazole can be used in the form of its acid addition salts in the form of aqueous or ethanolic solutions for the preparation of an aerosol for use in accordance with the invention. The preferred acid addition salt is dihydrochloride.
Vorrichtungen zur Erzeugung eines Dosieraerosols sind aus dem Stand der Technik zur Behandlung von Asthmaerkrankungen bekannt. Besonders bevorzugt ist eine Vorrichtung wie sie in der WO 91/14468 - Atomisiπg Devices and Methods -
offenbart ist. Der Vorteil der dort beschriebenen Vorrichtung ist es, daß auf die üblicherweise bei metered dose mhaiers (MDI's) erforderlichen Treibgase zur Erzeugung des Aerosols verzichtet werden kannDevices for generating a metered dose aerosol are known from the prior art for the treatment of asthma diseases. A device as described in WO 91/14468 - Atomization Devices and Methods - is particularly preferred. is disclosed. The advantage of the device described there is that the propellant gases usually required for metered dose mhaiers (MDI's) for producing the aerosol can be dispensed with
Alternativ zu einem Dosieraerosol kann Pramipexol auch mittels eines sogenannten Pulverinhalators appliziert werden, bei dem mikronisierte Teilchen in einem Bereich von 1 bis 15, bevorzugt 4 bis 8, μm des Wirkstoffes direkt als Pulver inhaliert werden.As an alternative to a metered dose aerosol, pramipexole can also be applied using a so-called powder inhaler, in which micronized particles in a range from 1 to 15, preferably 4 to 8, μm of the active ingredient are inhaled directly as a powder.
Erfindungsgemäß wird eine inhalative Einzeldosis zwischen 0.125 und 4,5 mg pro Patient vorgeschlagenAccording to the invention, an inhalation single dose between 0.125 and 4.5 mg per patient is proposed
Der nachfolgende Versuch belegt, daß durch die inhalative Applikation von Pramipexole im Tierexperiment bereits kurz nach der Inhalation hohe Plasmaspiegel erzielt werdenThe following experiment shows that inhalation of Pramipexole in animal experiments results in high plasma levels shortly after inhalation
Inhalative Einzeldosierung von 2 mg Pramipexole in 20 Mikroliter Wasser / HundInhaled single dose of 2 mg Pramipexole in 20 microliters of water / dog
Gewicht des Hundes (Beagle) 10 7 kgWeight of the dog (beagle) 10 7 kg
Narkosemittel-Anesthetic
Praemedikation Valium 7.5 mg i.mPremedication Valium 7.5 mg i.m.
Nembutal: 30 mg/kg i.v.Nembutal: 30 mg / kg IV
Die Applikation des Wirkstoffs erfolgte mittels Respimat Blutplasmaspiegel: Inhalation 2 mgThe active ingredient was administered by means of Respimat blood plasma level: inhalation 2 mg
Zeit (Min. nach Appl.) ng/mlTime (min. After appl.) Ng / ml
1.00 5.071.00 5.07
5.00 1.705.00 1.70
15.00 1.3515.00 1.35
45.00 0.9745.00 0.97
90.00 0.6890.00 0.68
120.00 0.64120.00 0.64
180.00 0.66
<_>180.00 0.66 <_>
Beispiel für die Herstellung einer InhalationslösungExample of the preparation of an inhalation solution
Beispiel 1example 1
10 %ige Lösung 2-Amino-6-n-propyl-amino-4,5,6,7-tetrahvdro-benzthιazol- dihvdrochlorid (Pramipexol)10% solution of 2-amino-6-n-propyl-amino-4,5,6,7-tetrahvdro-benzthιazol-dihvdrochloride (pramipexole)
SND 919 10 gSND 919 10 g
Zitronensäure 14 gCitric acid 14 g
Natriumphosphat sek. x 2H2O 6 gSodium phosphate sec. x 2H2O 6 g
Natriumpyrosulfit 2 gSodium pyrosulfite 2 g
Dest. Wasser ad 100 mlDistilled water to 100 ml
Herstellungsverfahrenproduction method
In ausgekochtem und unter Cθ2-Begasung abgekühltem Wasser werden nacheinander die Puffersubstanzen, die Wirksubstanz sowie Natriumpyrosulfit gelöst. Man füllt mit abgekochtem Wasser auf das gegebene Volumen auf und filtriert pyrogenfrei.The buffer substances, the active substance and sodium pyrosulfite are successively dissolved in boiled water and cooled with CO 2 gassing. Make up to the given volume with boiled water and filter without pyrogen.
Abfüllung: in braune Ampullen unterBottling: in brown ampoules under
SchutzgasShielding gas
Sterilisation: 20 Minuten bei 120°CSterilization: 20 minutes at 120 ° C
Die Herstellung und Abfüllung der Inhalationslösung muß in abgedunkelten Räumen vorgenommen werden.
The inhalation solution must be prepared and filled in darkened rooms.
Claims
Patentansprücheclaims
1 ) Verwendung von 2-Amino-6n-propyl-amιno-4,5.6,7-tetrahydrobenzothιazol, seines (-)-Enantiomeren sowie deren pharmakologisch verträgliche Säureadditionssalze zur mhalativen Behandlung von Krankheiten.1) Use of 2-amino-6n-propyl-amino-4,5,6,7-tetrahydrobenzothιazol, its (-) - enantiomer and their pharmacologically acceptable acid addition salts for the maltative treatment of diseases.
2) Verwendung von (-)-2-Amino-6n-propyl-amιno-4,5.6,7-tetrahydrobeπzothiazol sowie deren pharmakologisch verträglichen Säureadditionsalze zur inhalativen Behandlung von Krankheiten2) Use of (-) - 2-amino-6n-propyl-amino-4,5,6,7-tetrahydrobeπzothiazole and their pharmacologically acceptable acid addition salts for the inhalative treatment of diseases
3) Verwendung von (-)-2-Amino-6n-propyl-amιno-4,5.6 7-tetrahydrobenzothιazol- dihydrochlorid zur inhalativen Behandlung von Krankheiten3) Use of (-) - 2-amino-6n-propyl-amino-4,5,6 7-tetrahydrobenzothionazole dihydrochloride for the inhalative treatment of diseases
4) Verwendung nach Anspruch 1. 2 oder 3 zur inhalativen Behandlung der Parkinsonschen Erkrankung.4) Use according to claim 1, 2 or 3 for the inhalative treatment of Parkinson's disease.
5) Lösung enthaltend 2-Amino-6n-propyl-amιno-4,5,6,7-tetrahydrobenzothιazol1 sein (-)-Enantiomer sowie deren pharmakologisch verträgliche Säureadditionsalze für die inhalative Behandlung von Krankheiten.5) solution containing 2-amino-6n-propyl-amino-4,5,6,7-tetrahydrobenzothιazol 1 be its (-) - enantiomer and its pharmacologically acceptable acid addition salts for the inhalative treatment of diseases.
6) Dosieraerosol enthaltend einen pharmakologisch aktiven Wirkstoff zur Behandlung der Parkinsonschen Erkrankung6) MDI containing a pharmacologically active ingredient for the treatment of Parkinson's disease
7) Dosieraerosol nach Anspruch 6 dadurch gekennzeichnet, daß der Wirkstoff (-)2-Amino-6n-propyl-amino-4,5.6,7-tetrahydrobenzothiazo! sowie sein pharmakologisch verträgliches Säureadditionssalz ist7) MDI according to claim 6, characterized in that the active ingredient (-) 2-amino-6n-propyl-amino-4,5,6,7-tetrahydrobenzothiazo! as well as its pharmacologically acceptable acid addition salt
8) Mikronisiertes Pulver für die inhalative Behandlung enthaltend einen pharmakologisch aktiven Wirkstoff zur Behandlung der Parkinsonschen Erkrankung.8) Micronized powder for inhalation treatment containing a pharmacologically active ingredient for the treatment of Parkinson's disease.
9) Mikronisiertes Pulver nach Anspruch 8, dadurch gekennzeichnet, daß der Wirkstoff (-)-2-Amino-6n-propyl-amino-4,5, 6, 7-tetrahydrobenzothiazol sowie sein pharmakologisch verträgliches Säureadditionssalz ist.9) Micronized powder according to claim 8, characterized in that the active ingredient (-) - 2-amino-6n-propyl-amino-4,5, 6, 7-tetrahydrobenzothiazole and its pharmacologically acceptable acid addition salt.
10) Lösung enthaltend nach Anspruch 5, dadurch gekennzeichnet, daß sie zwischen 5 und 12 Gew. % (-)2-Amino-6n-propyl-amino-4,5,6,7-
tetrahydrobenzothiazol sowie sein pharmakologisch verträgliches Säureadditionssalz enthält.
10) Solution containing according to claim 5, characterized in that it between 5 and 12 wt.% (-) 2-amino-6n-propyl-amino-4,5,6,7- tetrahydrobenzothiazole and its pharmacologically acceptable acid addition salt contains.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU72856/96A AU7285696A (en) | 1995-10-04 | 1996-10-04 | Administration by inhalation of 2-amino-6n-propylamino-4,5,6,7-tetrahydrobenzothiazol, in particular of its (-)enantiomer and its pharmacologically tolerable acid addition salts |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19536916.5 | 1995-10-04 | ||
| DE19536916A DE19536916A1 (en) | 1995-10-04 | 1995-10-04 | Inhalative application of 2-amino-6n-propyl-amino-4,5,6,7-tetrahydrobenzothiazole, in particular its (-) - enantiomer, and their pharmacologically acceptable acid addition salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997012614A1 true WO1997012614A1 (en) | 1997-04-10 |
Family
ID=7773972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1996/004327 WO1997012614A1 (en) | 1995-10-04 | 1996-10-04 | Administration by inhalation of 2-amino-6n-propylamino-4,5,6,7-tetrahydrobenzothiazol, in particular of its (-)enantiomer and its pharmacologically tolerable acid addition salts |
Country Status (4)
| Country | Link |
|---|---|
| AU (1) | AU7285696A (en) |
| DE (1) | DE19536916A1 (en) |
| WO (1) | WO1997012614A1 (en) |
| ZA (1) | ZA968315B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19653969A1 (en) * | 1996-12-20 | 1998-06-25 | Boehringer Ingelheim Kg | New aqueous pharmaceutical preparation for the production of propellant-free aerosols |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2839431A1 (en) * | 1978-09-11 | 1980-03-20 | Dolorgiet Arzneimittelfabrik | Tranquilliser and hypertonic for heart and vascular disease treatment - contg. 1-(2-nitro-5-methylphenoxy)-3-tert.butyl-aminopropan-2-ol |
| EP0186087A1 (en) * | 1984-12-22 | 1986-07-02 | Dr. Karl Thomae GmbH | Tetrahydro-benzothiazoles, their production and their use as intermediates or drugs |
-
1995
- 1995-10-04 DE DE19536916A patent/DE19536916A1/en not_active Withdrawn
-
1996
- 1996-10-03 ZA ZA968315A patent/ZA968315B/en unknown
- 1996-10-04 WO PCT/EP1996/004327 patent/WO1997012614A1/en active Application Filing
- 1996-10-04 AU AU72856/96A patent/AU7285696A/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2839431A1 (en) * | 1978-09-11 | 1980-03-20 | Dolorgiet Arzneimittelfabrik | Tranquilliser and hypertonic for heart and vascular disease treatment - contg. 1-(2-nitro-5-methylphenoxy)-3-tert.butyl-aminopropan-2-ol |
| EP0186087A1 (en) * | 1984-12-22 | 1986-07-02 | Dr. Karl Thomae GmbH | Tetrahydro-benzothiazoles, their production and their use as intermediates or drugs |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA968315B (en) | 1997-04-04 |
| AU7285696A (en) | 1997-04-28 |
| DE19536916A1 (en) | 1997-04-10 |
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