GB1560406A - Solid solutions of ergot alkaholids in polymers - Google Patents
Solid solutions of ergot alkaholids in polymers Download PDFInfo
- Publication number
- GB1560406A GB1560406A GB42907/76A GB4290776A GB1560406A GB 1560406 A GB1560406 A GB 1560406A GB 42907/76 A GB42907/76 A GB 42907/76A GB 4290776 A GB4290776 A GB 4290776A GB 1560406 A GB1560406 A GB 1560406A
- Authority
- GB
- United Kingdom
- Prior art keywords
- composition
- polymer
- solid
- weight
- molecular weight
- 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
Links
- 229920000642 polymer Polymers 0.000 title claims description 46
- 239000006104 solid solution Substances 0.000 title claims description 26
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims description 52
- 229960003133 ergot alkaloid Drugs 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 16
- 239000003381 stabilizer Substances 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 12
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 12
- 238000001704 evaporation Methods 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 230000008020 evaporation Effects 0.000 claims description 9
- 239000007903 gelatin capsule Substances 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims description 6
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 239000008247 solid mixture Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 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 claims description 4
- 210000004051 gastric juice Anatomy 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- 239000008180 pharmaceutical surfactant Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 229920002261 Corn starch Polymers 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000008120 corn starch Substances 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920006324 polyoxymethylene Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 7
- 229920000036 polyvinylpyrrolidone Polymers 0.000 abstract description 6
- 239000001267 polyvinylpyrrolidone Substances 0.000 abstract description 6
- 235000013855 polyvinylpyrrolidone Nutrition 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
- 239000003826 tablet Substances 0.000 description 5
- 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
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 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
- 239000000945 filler Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 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
- 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
- UJYGDMFEEDNVBF-UHFFFAOYSA-N Ergocorninine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)C(C)C)C(C)C)C2)=C3C2=CNC3=C1 UJYGDMFEEDNVBF-UHFFFAOYSA-N 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
- 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
- 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
- 230000002708 enhancing effect Effects 0.000 description 1
- XQUUDUKVJKNJNP-OGGGUQDZSA-N ergocornine Chemical compound C([C@H]1N(C)C2)C([C]34)=CN=C4C=CC=C3C1=C[C@H]2C(=O)N[C@@]1(C(C)C)C(=O)N2[C@@H](C(C)C)C(=O)N3CCC[C@H]3[C@]2(O)O1 XQUUDUKVJKNJNP-OGGGUQDZSA-N 0.000 description 1
- OWEUDBYTKOYTAD-MKTPKCENSA-N ergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@@H]1C=C2C3=CC=CC4=NC=C([C]34)C[C@H]2N(C)C1)C(C)C)C1=CC=CC=C1 OWEUDBYTKOYTAD-MKTPKCENSA-N 0.000 description 1
- HEFIYUQVAZFDEE-UHFFFAOYSA-N ergocristinine Natural products N12C(=O)C(C(C)C)(NC(=O)C3C=C4C=5C=CC=C6NC=C(C=56)CC4N(C)C3)OC2(O)C2CCCN2C(=O)C1CC1=CC=CC=C1 HEFIYUQVAZFDEE-UHFFFAOYSA-N 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
- 150000002334 glycols Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 150000002689 maleic acids Chemical class 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
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1560406A true GB1560406A (en) | 1980-02-06 |
Family
ID=5959411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42907/76A Expired GB1560406A (en) | 1975-10-17 | 1976-10-15 | Solid solutions of ergot alkaholids in polymers |
Country Status (28)
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4450877A (en) * | 1977-11-03 | 1984-05-29 | Hoechst Aktiengesellschaft | Pharmaceutical preparations in solid unit dosage form |
| GB2160100A (en) * | 1984-06-14 | 1985-12-18 | Sandoz Ltd | Galenical retard formulations |
| AT383492B (de) * | 1981-06-24 | 1987-07-10 | Sandoz Ag | Verfahren zur herstellung von stabilen weichgelatinekapseln unter einsatz von fluessigen mutterkornalkaloidloesungen |
| US4992278A (en) * | 1987-01-14 | 1991-02-12 | Ciba-Geigy Corporation | Therapeutic system for sparingly soluble active ingredients |
| 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 |
| US6632455B2 (en) | 1997-12-22 | 2003-10-14 | Schering Corporation | Molecular dispersion composition with enhanced bioavailability |
| WO2005000273A1 (en) * | 2003-06-27 | 2005-01-06 | Bioprogress S.P.A. | Composite product obtainable by cogrinding of a active principle with a copolymer n-vinyl-2-pyrrolidone/vinyl-acetate |
| US7070968B2 (en) | 1994-02-04 | 2006-07-04 | Arch Development Corporation | DNA damaging agents in combination with tyrosine kinase inhibitors |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE442265B (sv) * | 1978-12-21 | 1985-12-16 | Sandoz Ag | Fast, enteral-overdragen komposition i enhetsform for oral tillforsel innehallande en ergotalkaloid |
| US4411882A (en) | 1978-12-21 | 1983-10-25 | Sandoz Ltd. | Galenical compositions |
| FR2454804B1 (fr) * | 1979-04-26 | 1986-11-21 | Sanofi Sa | Medicament a base de dihydroergotoxine et son procede de preparation |
| US4898729A (en) * | 1983-12-09 | 1990-02-06 | Euroceltique, S.A. | Treatment of hypertension, compounds and compositions for antihypertension and diuresis |
| 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 |
| 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 |
| WO2001039742A2 (en) * | 1999-12-03 | 2001-06-07 | Polichem S.A. | 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 |
| WO2016198983A1 (en) | 2015-06-09 | 2016-12-15 | Bend Research Inc. | Formulations to achieve rapid dissolution of drug from spray-dried dispersions in capsules |
| KR102882996B1 (ko) * | 2025-04-07 | 2025-11-07 | (주)휴마스 | 액체크로마토그래피와 막전도도 측정모듈 및 개량된 uv산화반응기를 이용하는 분획된 수중 탄소 및 질소 측정장치 및 이를 이용한 측정방법 |
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 FI FI762875A patent/FI762875A7/fi not_active Application Discontinuation
- 1976-10-08 DK DK454176A patent/DK146194C/da not_active IP Right Cessation
- 1976-10-08 NO NO763446A patent/NO144468C/no unknown
- 1976-10-08 SE SE7611189A patent/SE430379B/xx not_active IP Right Cessation
- 1976-10-13 NL NLAANVRAGE7611295,A patent/NL184558C/xx not_active IP Right Cessation
- 1976-10-14 CA CA263,423A patent/CA1079641A/en not_active Expired
- 1976-10-14 PH PH19008A patent/PH14513A/en unknown
- 1976-10-14 FR FR7630866A patent/FR2327764A1/fr active Granted
- 1976-10-15 SU SU762412401A patent/SU1165223A3/ru active
- 1976-10-15 GB GB42907/76A patent/GB1560406A/en not_active Expired
- 1976-10-15 ZA ZA00766166A patent/ZA766166B/xx unknown
- 1976-10-15 BE BE171578A patent/BE847368A/xx not_active IP Right Cessation
- 1976-10-15 NZ NZ182341A patent/NZ182341A/xx unknown
- 1976-10-15 CS CS766685A patent/CS199647B2/cs unknown
- 1976-10-15 HU HU76SA00002985A patent/HU172533B/hu not_active IP Right Cessation
- 1976-10-15 PT PT65719A patent/PT65719B/pt unknown
- 1976-10-15 AT AT767976A patent/AT362510B/de not_active IP Right Cessation
- 1976-10-15 ES ES452420A patent/ES452420A1/es not_active Expired
- 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 AU AU18754/76A patent/AU508628B2/en not_active Expired
- 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
-
1984
- 1984-12-30 MY MY63/84A patent/MY8400063A/xx unknown
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4450877A (en) * | 1977-11-03 | 1984-05-29 | Hoechst Aktiengesellschaft | Pharmaceutical preparations in solid unit dosage form |
| AT383492B (de) * | 1981-06-24 | 1987-07-10 | Sandoz Ag | Verfahren zur herstellung von stabilen weichgelatinekapseln unter einsatz von fluessigen mutterkornalkaloidloesungen |
| GB2160100A (en) * | 1984-06-14 | 1985-12-18 | Sandoz Ltd | Galenical retard formulations |
| US4992278A (en) * | 1987-01-14 | 1991-02-12 | Ciba-Geigy Corporation | Therapeutic system for sparingly soluble active ingredients |
| US7070968B2 (en) | 1994-02-04 | 2006-07-04 | Arch Development Corporation | DNA damaging agents in combination with tyrosine kinase inhibitors |
| US7838512B2 (en) | 1994-02-04 | 2010-11-23 | Arch Development Corporation | DNA damaging agents in combination with tyrosine kinase inhibitors |
| WO1999032118A1 (en) * | 1997-12-22 | 1999-07-01 | Schering Corporation | Molecular dispersion composition with enhanced bioavailability |
| AU761994B2 (en) * | 1997-12-22 | 2003-06-12 | Merck Sharp & Dohme Corp. | Molecular dispersion composition with enhanced bioavailability |
| US6632455B2 (en) | 1997-12-22 | 2003-10-14 | Schering Corporation | Molecular dispersion composition with enhanced bioavailability |
| AU761994C (en) * | 1997-12-22 | 2004-01-08 | Merck Sharp & Dohme Corp. | 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 |
| WO2005000273A1 (en) * | 2003-06-27 | 2005-01-06 | Bioprogress S.P.A. | Composite product obtainable by cogrinding of a active principle with a copolymer n-vinyl-2-pyrrolidone/vinyl-acetate |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |