IE43778B1 - Solid solutions of ergot alkaloids in polymers - Google Patents
Solid solutions of ergot alkaloids in polymersInfo
- Publication number
- IE43778B1 IE43778B1 IE2282/76A IE228276A IE43778B1 IE 43778 B1 IE43778 B1 IE 43778B1 IE 2282/76 A IE2282/76 A IE 2282/76A IE 228276 A IE228276 A IE 228276A IE 43778 B1 IE43778 B1 IE 43778B1
- Authority
- IE
- Ireland
- Prior art keywords
- composition
- polymer
- molecular weight
- solid
- weight
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims description 29
- 229960003133 ergot alkaloid Drugs 0.000 title claims description 17
- 239000006104 solid solution Substances 0.000 title claims description 17
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 11
- 239000003381 stabilizer Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 230000008020 evaporation Effects 0.000 claims description 6
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 210000004051 gastric juice Anatomy 0.000 claims description 3
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000008180 pharmaceutical surfactant Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229920006324 polyoxymethylene Polymers 0.000 claims 1
- 230000000063 preceeding effect Effects 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 abstract description 6
- 239000001267 polyvinylpyrrolidone Substances 0.000 abstract description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- 150000003839 salts Chemical class 0.000 abstract description 3
- 239000011343 solid material Substances 0.000 abstract 2
- 229930015720 peptide alkaloid Natural products 0.000 abstract 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000007903 gelatin capsule Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000008247 solid mixture Substances 0.000 description 4
- 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 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 229960004704 dihydroergotamine Drugs 0.000 description 3
- HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- -1 methanesulphonic Chemical class 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- BGHDUTQZGWOQIA-VQSKNWBGSA-N Ergovaline Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)C(C)C)C)C2)=C3C2=CNC3=C1 BGHDUTQZGWOQIA-VQSKNWBGSA-N 0.000 description 1
- LFPHMXIOQBBTSS-UHFFFAOYSA-N Galetin Natural products C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 LFPHMXIOQBBTSS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 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 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- YDOTUXAWKBPQJW-UHFFFAOYSA-N alpha-Ergocryptinine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-UHFFFAOYSA-N 0.000 description 1
- YDOTUXAWKBPQJW-NSLWYYNWSA-N alpha-ergocryptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-NSLWYYNWSA-N 0.000 description 1
- 229950001817 alpha-ergocryptine Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 229960004943 ergotamine Drugs 0.000 description 1
- OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 description 1
- XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 description 1
- BGHDUTQZGWOQIA-RKUMIMICSA-N ergovaline Natural products O=C(N[C@@]1(C)C(=O)N2[C@H](C(C)C)C(=O)N3[C@@H]([C@]2(O)O1)CCC3)[C@@H]1C=C2[C@H](N(C)C1)Cc1c3c([nH]c1)cccc23 BGHDUTQZGWOQIA-RKUMIMICSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 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
- A61K31/435—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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/48—Ergoline derivatives, e.g. lysergic acid, ergotamine
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2546577A DE2546577B2 (de) | 1975-10-17 | 1975-10-17 | Feste Stoffe aus Polyvinylpyrrolidon und Ergotalkaloiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43778L IE43778L (en) | 1977-04-17 |
| IE43778B1 true IE43778B1 (en) | 1981-05-20 |
Family
ID=5959411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2282/76A IE43778B1 (en) | 1975-10-17 | 1976-10-15 | Solid solutions of ergot alkaloids in polymers |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS5854122B2 (nl) |
| AT (1) | AT362510B (nl) |
| AU (1) | AU508628B2 (nl) |
| BE (1) | BE847368A (nl) |
| CA (1) | CA1079641A (nl) |
| CH (1) | CH643737A5 (nl) |
| CS (1) | CS199647B2 (nl) |
| DE (1) | DE2546577B2 (nl) |
| DK (1) | DK146194C (nl) |
| ES (1) | ES452420A1 (nl) |
| FI (1) | FI762875A (nl) |
| FR (1) | FR2327764A1 (nl) |
| GB (1) | GB1560406A (nl) |
| GR (1) | GR61268B (nl) |
| HK (1) | HK3183A (nl) |
| HU (1) | HU172533B (nl) |
| IE (1) | IE43778B1 (nl) |
| IL (1) | IL50686A (nl) |
| MY (1) | MY8400063A (nl) |
| NL (1) | NL184558C (nl) |
| NO (1) | NO144468C (nl) |
| NZ (1) | NZ182341A (nl) |
| PH (1) | PH14513A (nl) |
| PT (1) | PT65719B (nl) |
| SE (1) | SE430379B (nl) |
| SG (1) | SG63082G (nl) |
| SU (1) | SU1165223A3 (nl) |
| ZA (1) | ZA766166B (nl) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1572226A (en) * | 1977-11-03 | 1980-07-30 | Hoechst Uk Ltd | Pharmaceutical preparations in solid unit dosage form |
| US4411882A (en) | 1978-12-21 | 1983-10-25 | Sandoz Ltd. | Galenical compositions |
| DK154607C (da) * | 1978-12-21 | 1989-06-05 | Sandoz Ag | Fremgangsmaade til fremstilling af en laegemiddelform til oral administration af ergotalkaloider |
| FR2454804B1 (fr) * | 1979-04-26 | 1986-11-21 | Sanofi Sa | Medicament a base de dihydroergotoxine et son procede de preparation |
| US4366145A (en) * | 1981-06-24 | 1982-12-28 | Sandoz, Inc. | Soft gelatin capsule with a liquid ergot alkaloid center fill solution and method of preparation |
| US4898729A (en) * | 1983-12-09 | 1990-02-06 | Euroceltique, S.A. | Treatment of hypertension, compounds and compositions for antihypertension and diuresis |
| NL194389C (nl) * | 1984-06-14 | 2002-03-04 | Novartis Ag | Werkwijze voor het bereiden van een vaste dispersie van een farmaceutisch actief middel dat een lage oplosbaarheid in water heeft, in een vaste matrix van een in water oplosbaar polyalkyleenglycol als drager. |
| ATE72111T1 (de) * | 1987-01-14 | 1992-02-15 | Ciba Geigy Ag | Therapeutisches system fuer schwerloesliche wirkstoffe. |
| FR2610827B1 (fr) * | 1987-02-18 | 1991-09-13 | Pf Medicament | Comprime de dihydroergotamine (d.h.e.) du type a matrice hydrophile et son procede de fabrication |
| US5064656A (en) * | 1989-11-14 | 1991-11-12 | Dr. Gergely & Co. | Uncoated pharmaceutical reaction tablet |
| DE4401646A1 (de) * | 1994-01-21 | 1995-07-27 | Krewel Werke Gmbh | Optimal freisetzende Kava-Extrakte |
| US6524832B1 (en) | 1994-02-04 | 2003-02-25 | Arch Development Corporation | DNA damaging agents in combination with tyrosine kinase inhibitors |
| US6632455B2 (en) | 1997-12-22 | 2003-10-14 | Schering Corporation | Molecular dispersion composition with enhanced bioavailability |
| WO1999032118A1 (en) * | 1997-12-22 | 1999-07-01 | Schering Corporation | Molecular dispersion composition with enhanced bioavailability |
| US6316462B1 (en) | 1999-04-09 | 2001-11-13 | Schering Corporation | Methods of inducing cancer cell death and tumor regression |
| MXPA02005291A (es) * | 1999-12-03 | 2004-06-21 | Polichem Sa | Metodos para elaborar composiciones farmaceuticas de liberacion sostenida de alcaloides de cornezuelo de centeno que tienen biodisponibilidad mejorada y composiciones de los mismos. |
| US7771746B2 (en) | 1999-12-03 | 2010-08-10 | Polichem Sa | Methods for making sustained-release pharmaceutical compositions of ergot alkaloids having improved bioavailability and compositions thereof |
| US7135436B2 (en) | 2003-05-05 | 2006-11-14 | J.F. Daley International, Ltd. | Solid algicide, preparation and usage in recirculating water |
| US20060141038A1 (en) * | 2003-06-27 | 2006-06-29 | Bioprogress S. P. A. | Composite product obtainable by cogrinding of a active principle with a copolymer n-vinyl-2 pyrrolidone/vinyl-acetate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1175430A (en) * | 1966-04-07 | 1969-12-23 | Sandoz Ltd | Pharmaceutical Compositions containing Ergot Alkaloids |
-
1975
- 1975-10-17 DE DE2546577A patent/DE2546577B2/de not_active Withdrawn
-
1976
- 1976-10-01 CH CH1244876A patent/CH643737A5/de not_active IP Right Cessation
- 1976-10-08 SE SE7611189A patent/SE430379B/xx not_active IP Right Cessation
- 1976-10-08 NO NO763446A patent/NO144468C/no unknown
- 1976-10-08 FI FI762875A patent/FI762875A/fi not_active Application Discontinuation
- 1976-10-08 DK DK454176A patent/DK146194C/da not_active IP Right Cessation
- 1976-10-13 NL NLAANVRAGE7611295,A patent/NL184558C/nl not_active IP Right Cessation
- 1976-10-14 PH PH19008A patent/PH14513A/en unknown
- 1976-10-14 FR FR7630866A patent/FR2327764A1/fr active Granted
- 1976-10-14 CA CA263,423A patent/CA1079641A/en not_active Expired
- 1976-10-15 ZA ZA00766166A patent/ZA766166B/xx unknown
- 1976-10-15 CS CS766685A patent/CS199647B2/cs unknown
- 1976-10-15 BE BE171578A patent/BE847368A/xx not_active IP Right Cessation
- 1976-10-15 AU AU18754/76A patent/AU508628B2/en not_active Expired
- 1976-10-15 SU SU762412401A patent/SU1165223A3/ru active
- 1976-10-15 AT AT767976A patent/AT362510B/de not_active IP Right Cessation
- 1976-10-15 NZ NZ182341A patent/NZ182341A/xx unknown
- 1976-10-15 PT PT65719A patent/PT65719B/pt unknown
- 1976-10-15 IE IE2282/76A patent/IE43778B1/en not_active IP Right Cessation
- 1976-10-15 IL IL50686A patent/IL50686A/xx unknown
- 1976-10-15 ES ES452420A patent/ES452420A1/es not_active Expired
- 1976-10-15 GB GB42907/76A patent/GB1560406A/en not_active Expired
- 1976-10-15 HU HU76SA00002985A patent/HU172533B/hu not_active IP Right Cessation
- 1976-10-16 JP JP51123463A patent/JPS5854122B2/ja not_active Expired
- 1976-10-16 GR GR51952A patent/GR61268B/el unknown
-
1982
- 1982-12-23 SG SG630/82A patent/SG63082G/en unknown
-
1983
- 1983-01-20 HK HK31/83A patent/HK3183A/xx unknown
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1984
- 1984-12-30 MY MY63/84A patent/MY8400063A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |