PT77467B - Neue orale mopidamolformen - Google Patents
Neue orale mopidamolformen Download PDFInfo
- Publication number
- PT77467B PT77467B PT77467A PT7746783A PT77467B PT 77467 B PT77467 B PT 77467B PT 77467 A PT77467 A PT 77467A PT 7746783 A PT7746783 A PT 7746783A PT 77467 B PT77467 B PT 77467B
- Authority
- PT
- Portugal
- Prior art keywords
- adjuvants
- mopidamol
- acid
- process according
- active ingredient
- Prior art date
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- FOYWNSCCNCUEPU-UHFFFAOYSA-N mopidamol Chemical group C12=NC(N(CCO)CCO)=NC=C2N=C(N(CCO)CCO)N=C1N1CCCCC1 FOYWNSCCNCUEPU-UHFFFAOYSA-N 0.000 title claims description 16
- 229950010718 mopidamol Drugs 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 8
- 239000002671 adjuvant Substances 0.000 claims 19
- 238000000034 method Methods 0.000 claims 13
- 230000002378 acidificating effect Effects 0.000 claims 8
- 239000004480 active ingredient Substances 0.000 claims 8
- 239000011324 bead Substances 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 239000011248 coating agent Substances 0.000 claims 5
- 238000000576 coating method Methods 0.000 claims 5
- 239000008187 granular material Substances 0.000 claims 5
- 239000004922 lacquer Substances 0.000 claims 5
- 239000003826 tablet Substances 0.000 claims 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 4
- -1 2,6-bis (diethylamino) -4-piperidinopyrimido [4,5-d] pyrimidine Chemical compound 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- 239000000654 additive Substances 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 239000007903 gelatin capsule Substances 0.000 claims 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 239000001530 fumaric acid Substances 0.000 claims 2
- 239000000314 lubricant Substances 0.000 claims 2
- 239000011049 pearl Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- 238000005550 wet granulation Methods 0.000 claims 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- UYUXSRADSPPKRZ-UHFFFAOYSA-N D-glucuronic acid gamma-lactone Natural products O=CC(O)C1OC(=O)C(O)C1O UYUXSRADSPPKRZ-UHFFFAOYSA-N 0.000 claims 1
- UYUXSRADSPPKRZ-SKNVOMKLSA-N D-glucurono-6,3-lactone Chemical compound O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O UYUXSRADSPPKRZ-SKNVOMKLSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 229920002125 Sokalan® Polymers 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 229960003403 betaine hydrochloride Drugs 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 238000007908 dry granulation Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003925 fat Substances 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 235000011087 fumaric acid Nutrition 0.000 claims 1
- 229950002441 glucurolactone Drugs 0.000 claims 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 239000008188 pellet Substances 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 159000000001 potassium salts Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000003232 water-soluble binding agent Substances 0.000 claims 1
- 239000007853 buffer solution Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Descrição das Figuras;
Figura 1:
Velocidade de libertação in vitro de comprimidos de mopidamol revestidos, com várias quantidades de citrato de sódio primário em solução tampão diluída com píl 6 (250 mg de mopidamol/comprimldo)
Figura 2:
Níveis médios de mopidamol no plasma
W = 6.
Figura 3:
nVelocidade de libertação in vitro de co prirnidos de mopidamol revestidos, com várias quantidades de ácido em solução tampão diluída com pH 4 (250 mg de mopidamol/comprimido) .
23
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.· -' ..<·
Claims (4)
1·
·'·?
Ϊ4
:ν.
γ
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444
1, caracterizado por nestas novas formas de mopidamol se incorporar para 1 mol de mopidamol pelo menos 1 vai de um adjuvante oralmente assimilável, e eventualmente também aditivos usuais.
-
(2, 6-bis(d.ietanolam.ino)-4-piperidinbpirimido-/“5, 4-d__7pir.imid.ina paru pelo menos 1 vai de um adjuvante de reacção ácida, eventualmente na presen· ça de um aglutinante, após o que a mistura é comprimida por meio de prensas para comprimidos ou compactad-ires de cilindros ou é granulada a liúmido ou a seco e nova-rente triturada, eventualmente após adição de outros adjuvantes, ou então a mistura é processada em forma de pérolas ou directamente
prensada em comprimidos na presença de outros adjuvantes, podendo eventualmente os grânulos, pérolas ou comprimidos serem cobertos por uma laca reguladora da libertação do ingrediente activo ou uma cobertura correctora de gosto, e podendo opcionalmante os grânulos ou pérolas serem introduzidos em cápsulas.
- 22 _
Processo de acordo com a reivindicação
3£
Processo de acordo com as reivindicações 1 e 2, caracterizado por nestas formas se incorporar para 1 mol de mopidamol 1 a 8 vai de um adjuvante ácido oralmente assimilável.
- 24 PftÇTUGAI
4& Processo de acordo com as reivindicações 1 a 5» caracterizddo por se utilizarem como adjuvantes ácidos o ácido tartárico, o ácido cítrico, o ácido fumárico, o ácido succínico, o ácido málico, o ácido ascórbico, o ácido adípico, os sais ácidos sódico e potássico destes ácidos, o cloridrato de betaína, os anidridos de ácido succínico que hidrolisam em água dando ácidos, o ácido glutárico ou a D-glucurono-^ -lactona, ou misturas destes adjuvantes ácidos.
- 5â Processo de acordo com as reivindicações 1 a 3, caracterizado por se utilizar como adjuvante áci do o ácido fumárico.
- 6a Processo de acordo com as reivindicações 1 a 5, caracterizado por o mopidamol ser intimamente misturado com os adjuvantes ácidos, em forma de granulado com um diâmetro de partículas compreendido entre 0,1 e 2,0 mm, de preferência 0,25 e 1,25 mm, sendo os grânulos, que eventualmente foram antes cobertos por uma laca retardadora, eventualmente introduzidos em cápsulas de gelatina dura.
- 78 Processo de acordo com as reivindicações 1 a 5, caracterizado por o mopidamol ser misturado com os adjuvantes ácidos, em forma de pérolas com um diâmetro de 0,1 a 2,0 mm, de preferência 0,5 a 1,5 mm, sendo as pérolas, que eventualmente foram antes cobertas por uma laca retardadô ra, eventualmente introduzidas em cápsulas de gelatina dura.
- 25 _
·.'·
• ν' V.
• * . .....
•5:
·' t
V
•·\
Λ·
- 8S Processo de acordo com as reivindicações 1 a 6, caracterizado por se incorporar no mopidamol e nos adjuvantes ácidos, aglutinantes solúveis etis água e/ou adjuvantes formadores de muco, mas em especial solubilizantes
·. V
9'·
Processo de acordo com a reivindicação 8, caracterizado por as misturas incorporando o ingrediente activo, adjuvantes ácidos, eventuais solubilizantee e outros adjuvantes habituais, serem prensados e granuladas na presença de celulose metilica, etílica, hidroxietílica ou hidropropilmetílica, de ácidos poliacrílicos ou de gorduras.
- loa -
Ύ.
Ρχ-ocesso de acordo com as reivindicações 1 a 9, caracterizado por o ingrediente activo ser processado com. um ou mais adjuvantes ácidos, com outros adjuvantes directamente prensáveis e com lubrificantes para se obter uma mistura directamente prensâvel em comprimidos, sendo esta mistura, após prensagem em núcleos de comprimidos, coberta com uma cobertura correctora de gosto.
>/
- lia Processo de acordo com as reivindicações 1 a 9, caracterizado por o ingrediente activo, em conjunto com um ou mais adjuvantes ácidos, ser convertido em
granulado por meio de granulação a húmido ou a seco, sendo
este granulado, após adição de outros adjuvantes, prensado
26
em núcleos cobertos por uma cobertura correctora de gosto, gue evaatualmente também liberta lentamente o ingrediente
activo.
- 122 Processo de acordo com os reivindicações 1 a 9, caracterizado por o ingrediente activo, em conjunto com adjuvantes usuais, ser convertido n granu1~do por meio de granulação a húmido ou a seco, sendo >ctc yr;< miado, após adição de um ou mais adjuvantes ácidos · do lubrificante, prensado em núcleos cobertos por uma cob.-rtura ocrrectora do gosto, gtie eventualmente também liberta lentamante o ingrediente activo.
- 13a Ρχ-ocesso de acordo com as reivindicações 1 a 7 ou 10 a 12, caracterizado por as·, formas da mopidamol apresentarem urna cobertura da laca gue lib rta pelo menos 90% do ingrediente activo no tracto yastro-intestinal distribuído por um período de 2 horas.
Processo de acordo com 3·ι reivindicações 1 a 13, caracterizado por o solubi1izantu conter glicerina de ácido gordo-éster de polietilenoglicol,
- 152 _
Processo de acordo com as reivindicações 1 a 9, caracterizado por uma parte do adjuvante ácido
27
/.'Λ
4·:··
.·
ser revestida por uma cobertura de celulose bidroxietílica ou hidroxipropilmetílica onde são aplicados o ingrediente activo e os restantes aditivos, sendo as pérolas assim obtidas revestidas, se desejado, por uma laca e/ou as pérolas assim preparadas eventualmente introduzidas em cápsulas de gelatina dura.
A requerente declara que o primeiro pedido desta patente foi depositado na República Federal Alemã, em 9 de Outubro de 1982, sob o ns Γ- 32 37 575.1.
·:
•λ’·:
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823237575 DE3237575A1 (de) | 1982-10-09 | 1982-10-09 | Neue orale mopidamolformen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT77467A PT77467A (de) | 1983-11-01 |
| PT77467B true PT77467B (de) | 1986-05-07 |
Family
ID=6175408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT77467A PT77467B (de) | 1982-10-09 | 1983-10-07 | Neue orale mopidamolformen |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4596705A (pt) |
| EP (1) | EP0108898B1 (pt) |
| JP (1) | JPH07558B2 (pt) |
| AT (1) | ATE21481T1 (pt) |
| AU (1) | AU560251B2 (pt) |
| CA (1) | CA1228546A (pt) |
| DE (2) | DE3237575A1 (pt) |
| DK (1) | DK158541C (pt) |
| ES (1) | ES8500743A1 (pt) |
| FI (1) | FI79650C (pt) |
| GB (1) | GB2128088B (pt) |
| GR (1) | GR79015B (pt) |
| IE (1) | IE56058B1 (pt) |
| IL (1) | IL69930A (pt) |
| NO (1) | NO833638L (pt) |
| NZ (1) | NZ205894A (pt) |
| PT (1) | PT77467B (pt) |
| ZA (1) | ZA837499B (pt) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3237575A1 (de) * | 1982-10-09 | 1984-04-12 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue orale mopidamolformen |
| GB8414220D0 (en) * | 1984-06-04 | 1984-07-11 | Sterwin Ag | Medicaments in unit dose form |
| GB8524001D0 (en) * | 1985-09-30 | 1985-11-06 | Glaxo Group Ltd | Pharmaceutical composition |
| CA1323833C (en) * | 1987-04-28 | 1993-11-02 | Yatindra M. Joshi | Pharmaceutical compositions in the form of beadlets and method |
| US5364646A (en) * | 1990-01-10 | 1994-11-15 | Dr. Karl Thomae Gmbh | Oral pharmaceutical forms of pimobendan |
| CA2039742A1 (en) * | 1990-04-23 | 1991-10-24 | Andrew B. Dennis | Tablet composition and method for problem pharmaceutical materials |
| US5156845A (en) * | 1990-05-04 | 1992-10-20 | Colgate-Palmolive Company | Dry mouth lozenge |
| US5523289A (en) * | 1991-04-15 | 1996-06-04 | Abbott Laboratories | Pharmaceutical composition |
| EP0585355B1 (en) * | 1991-05-20 | 1995-03-22 | Marion Laboratories, Inc. | Multi-layered controlled release formulation |
| EP1093814A1 (en) * | 1999-10-22 | 2001-04-25 | Boehringer Ingelheim Pharma KG | Use of dipyridamole or mopidamol in the manufacture of a medicament for the treatment and prevention of fibrin-dependent microcirculation disorders |
| US7089934B2 (en) * | 2000-02-28 | 2006-08-15 | Vectura Limited | Delivery of oral drugs |
| US7064130B2 (en) * | 2001-04-20 | 2006-06-20 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Use of radical-scavenging compounds for treatment and prevention of NO-dependent microcirculation disorders |
| US20030181488A1 (en) | 2002-03-07 | 2003-09-25 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Administration form for the oral application of 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester and the salts thereof |
| AU2002350719A1 (en) * | 2002-11-29 | 2004-06-23 | Janssen Pharmaceutica N.V. | Pharmaceutical compositions comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base |
| CN1747734A (zh) * | 2003-02-07 | 2006-03-15 | 贝林格尔·英格海姆国际有限公司 | 潘生丁或单哌潘生丁在治疗和预防mmp－9－依赖性疾病中的用途 |
| AU2004231306A1 (en) | 2003-04-24 | 2004-11-04 | Boehringer Ingelheim International Gmbh | Use of dipyridamole or mopidamole for treatment and prevention of thrombo-embolic diseases and disorders caused by excessive formation of thrombin and/or by elevated expression of thrombin receptors |
| US8709476B2 (en) * | 2003-11-04 | 2014-04-29 | Supernus Pharmaceuticals, Inc. | Compositions of quaternary ammonium compounds containing bioavailability enhancers |
| DK2210605T3 (en) * | 2003-11-04 | 2017-05-22 | Tcd Royalty Sub Llc | Daily single dose doses of trospium. |
| DE102004011512B4 (de) | 2004-03-08 | 2022-01-13 | Boehringer Ingelheim Vetmedica Gmbh | Pharmazeutische Zubereitung enthaltend Pimobendan |
| EP1579862A1 (en) | 2004-03-25 | 2005-09-28 | Boehringer Ingelheim Vetmedica Gmbh | Use of PDE III inhibitors for the reduction of heart size in mammals suffering from heart failure |
| US8980894B2 (en) | 2004-03-25 | 2015-03-17 | Boehringer Ingelheim Vetmedica Gmbh | Use of PDE III inhibitors for the treatment of asymptomatic (occult) heart failure |
| EP2559430B1 (en) | 2005-03-22 | 2015-06-24 | Losan Pharma GmbH | Solubilized Ibuprofen |
| EP1915137B8 (de) * | 2005-08-10 | 2013-09-11 | ADD Advanced Drug Delivery Technologies, Ltd. | Orales präparat mit kontrollierter freisetzung |
| RU2428176C2 (ru) * | 2006-01-27 | 2011-09-10 | Юранд, Инк. | Системы доставки лекарственного средства, содержащие слабоосновные лекарственные средства и органические кислоты |
| CN103211779B (zh) * | 2006-01-27 | 2016-03-16 | 阿代尔制药股份有限公司 | 包含弱碱性选择性5-羟色胺5-ht3阻断剂和有机酸的药物递送系统 |
| US7731604B2 (en) * | 2006-10-31 | 2010-06-08 | Taylor Made Golf Company, Inc. | Golf club iron head |
| EP1920785A1 (en) | 2006-11-07 | 2008-05-14 | Boehringer Ingelheim Vetmedica Gmbh | Liquid preparation comprising a complex of pimobendan and cyclodextrin |
| UA97813C2 (uk) * | 2006-12-05 | 2012-03-26 | Янссен Фармацевтика Н.В. | Фумаратна сіль (альфа s, бета r)-6-бром-альфа-[2-(диметиламіно)етил]-2-метоксі-альфа-1-нафталеніл-бета-феніл-3-хінолінетанолу |
| US8133506B2 (en) * | 2008-03-12 | 2012-03-13 | Aptalis Pharmatech, Inc. | Drug delivery systems comprising weakly basic drugs and organic acids |
| CN102223882B (zh) | 2008-11-25 | 2016-02-03 | 贝林格尔.英格海姆维特梅迪卡有限公司 | 用于治疗肥厚型心肌病的III 型磷酸二酯酶(PPE III)抑制剂或Ca2+敏化剂 |
| US20110003005A1 (en) * | 2009-07-06 | 2011-01-06 | Gopi Venkatesh | Methods of Treating PDNV and PONV with Extended Release Ondansetron Compositions |
| EP3167876B1 (en) | 2012-03-15 | 2021-09-08 | Boehringer Ingelheim Vetmedica GmbH | Pharmaceutical tablet formulation for the veterinary medical sector, method of production and use thereof |
| MY183976A (en) * | 2012-09-19 | 2021-03-17 | Taiho Pharmaceutical Co Ltd | Pharmaceutical composition for oral administration with improved dissolution and/or absorption |
| EP3021832B9 (en) | 2013-07-19 | 2023-03-15 | Boehringer Ingelheim Vetmedica GmbH | Preserved etherified cyclodextrin derivatives containing liquid aqueous pharmaceutical composition |
| CA2930033C (en) | 2013-12-04 | 2022-12-13 | Boehringer Ingelheim Vetmedica Gmbh | Improved pharmaceutical compositions of pimobendan |
| JP6525897B2 (ja) * | 2016-01-21 | 2019-06-05 | 日清オイリオグループ株式会社 | タブレットの硬度調整剤 |
| US10537570B2 (en) | 2016-04-06 | 2020-01-21 | Boehringer Ingelheim Vetmedica Gmbh | Use of pimobendan for the reduction of heart size and/or the delay of onset of clinical symptoms in patients with asymptomatic heart failure due to mitral valve disease |
| CN109942445A (zh) * | 2019-02-26 | 2019-06-28 | 山东瑞弘生物科技有限公司 | 甜菜碱盐酸盐合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322755A (en) | 1964-03-10 | 1967-05-30 | Boehringer Sohn Ingelheim | Basic-substituted 1, 2, 3, 4-tetrahydropyrimido [5, 4-d]-pyrimidines |
| DD146547A5 (de) * | 1978-07-15 | 1981-02-18 | Boehringer Sohn Ingelheim | Arzneimittel-retardform mit unloeslichen poroesen diffusionshuellen |
| EP0019586A1 (de) * | 1979-05-11 | 1980-11-26 | Ciba-Geigy Ag | Neue antithrombotische Kombinationspräparate |
| DE2931573A1 (de) * | 1979-08-03 | 1981-02-26 | Thomae Gmbh Dr K | Mittel zur bekaempfung des wachstums von krebszellen und dessen herstellung |
| DE3000979A1 (de) * | 1980-01-12 | 1981-07-23 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue dipyridamol-retardformen und verfahren zu ihrer herstellung |
| DE3124090A1 (de) * | 1981-06-19 | 1983-01-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue orale dipyridamolformen |
| DE3126703A1 (de) * | 1981-07-07 | 1983-01-27 | Dr. Karl Thomae Gmbh, 7950 Biberach | Bromhexin-retardform und verfahren zu ihrer herstellung |
| DE3237575A1 (de) * | 1982-10-09 | 1984-04-12 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue orale mopidamolformen |
-
1982
- 1982-10-09 DE DE19823237575 patent/DE3237575A1/de not_active Withdrawn
-
1983
- 1983-09-24 DE DE8383109510T patent/DE3365465D1/de not_active Expired
- 1983-09-24 AT AT83109510T patent/ATE21481T1/de not_active IP Right Cessation
- 1983-09-24 EP EP83109510A patent/EP0108898B1/de not_active Expired
- 1983-10-05 FI FI833605A patent/FI79650C/fi not_active IP Right Cessation
- 1983-10-06 DK DK460683A patent/DK158541C/da not_active IP Right Cessation
- 1983-10-06 NO NO833638A patent/NO833638L/no unknown
- 1983-10-07 US US06/539,998 patent/US4596705A/en not_active Expired - Lifetime
- 1983-10-07 NZ NZ205894A patent/NZ205894A/en unknown
- 1983-10-07 PT PT77467A patent/PT77467B/pt not_active IP Right Cessation
- 1983-10-07 ES ES526331A patent/ES8500743A1/es not_active Expired
- 1983-10-07 GB GB08326877A patent/GB2128088B/en not_active Expired
- 1983-10-07 JP JP58188283A patent/JPH07558B2/ja not_active Expired - Lifetime
- 1983-10-07 IL IL69930A patent/IL69930A/xx not_active IP Right Cessation
- 1983-10-07 GR GR72641A patent/GR79015B/el unknown
- 1983-10-07 AU AU19985/83A patent/AU560251B2/en not_active Ceased
- 1983-10-07 IE IE2358/83A patent/IE56058B1/en not_active IP Right Cessation
- 1983-10-07 CA CA000438670A patent/CA1228546A/en not_active Expired
- 1983-10-07 ZA ZA837499A patent/ZA837499B/xx unknown
-
1985
- 1985-09-03 US US06/772,166 patent/US4650664A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB2128088A (en) | 1984-04-26 |
| DE3365465D1 (en) | 1986-09-25 |
| US4596705A (en) | 1986-06-24 |
| IL69930A (en) | 1986-08-31 |
| FI79650B (fi) | 1989-10-31 |
| JPS5989615A (ja) | 1984-05-23 |
| EP0108898B1 (de) | 1986-08-20 |
| FI79650C (fi) | 1990-02-12 |
| IL69930A0 (en) | 1984-01-31 |
| NZ205894A (en) | 1986-08-08 |
| DK460683D0 (da) | 1983-10-06 |
| FI833605L (fi) | 1984-04-10 |
| DK158541B (da) | 1990-06-05 |
| ZA837499B (en) | 1985-06-26 |
| AU1998583A (en) | 1984-04-12 |
| JPH07558B2 (ja) | 1995-01-11 |
| EP0108898A1 (de) | 1984-05-23 |
| IE832358L (en) | 1984-04-09 |
| ES526331A0 (es) | 1984-11-01 |
| ES8500743A1 (es) | 1984-11-01 |
| GB8326877D0 (en) | 1983-11-09 |
| US4650664A (en) | 1987-03-17 |
| AU560251B2 (en) | 1987-04-02 |
| GB2128088B (en) | 1986-04-30 |
| GR79015B (pt) | 1984-10-02 |
| DK158541C (da) | 1990-11-05 |
| DK460683A (da) | 1984-04-10 |
| FI833605A0 (fi) | 1983-10-05 |
| CA1228546A (en) | 1987-10-27 |
| IE56058B1 (en) | 1991-04-10 |
| NO833638L (no) | 1984-04-10 |
| DE3237575A1 (de) | 1984-04-12 |
| PT77467A (de) | 1983-11-01 |
| ATE21481T1 (de) | 1986-09-15 |
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| MM3A | Annulment or lapse |
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