CA1063936A - Preparation of amorphous solid of macrolide antibiotics - Google Patents
Preparation of amorphous solid of macrolide antibioticsInfo
- Publication number
- CA1063936A CA1063936A CA249,607A CA249607A CA1063936A CA 1063936 A CA1063936 A CA 1063936A CA 249607 A CA249607 A CA 249607A CA 1063936 A CA1063936 A CA 1063936A
- Authority
- CA
- Canada
- Prior art keywords
- cellulose
- amorphous solid
- macrolide
- antibiotic
- macrolide antibiotic
- 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
- 239000007787 solid Substances 0.000 title claims abstract description 43
- 239000003120 macrolide antibiotic agent Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title description 4
- 238000001694 spray drying Methods 0.000 claims abstract description 21
- 229920000642 polymer Polymers 0.000 claims abstract description 19
- 229920002678 cellulose Polymers 0.000 claims abstract description 15
- 239000001913 cellulose Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 13
- 239000001856 Ethyl cellulose Substances 0.000 claims description 11
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical group CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 11
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 11
- 229920001249 ethyl cellulose Polymers 0.000 claims description 11
- 230000003115 biocidal effect Effects 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 5
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 5
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 5
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 5
- 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 description 5
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 4
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 3
- 229940071676 hydroxypropylcellulose Drugs 0.000 claims description 3
- 229960001701 chloroform Drugs 0.000 claims 3
- 239000000126 substance Substances 0.000 abstract description 22
- 230000000087 stabilizing effect Effects 0.000 abstract description 17
- 239000013078 crystal Substances 0.000 description 13
- 239000007921 spray Substances 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 238000003860 storage Methods 0.000 description 10
- 239000000463 material Substances 0.000 description 7
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- DMUAPQTXSSNEDD-QALJCMCCSA-N Midecamycin Chemical compound C1[C@](O)(C)[C@@H](OC(=O)CC)[C@H](C)O[C@H]1O[C@H]1[C@H](N(C)C)[C@@H](O)[C@H](O[C@@H]2[C@H]([C@H](OC(=O)CC)CC(=O)O[C@H](C)C/C=C/C=C/[C@H](O)[C@H](C)C[C@@H]2CC=O)OC)O[C@@H]1C DMUAPQTXSSNEDD-QALJCMCCSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 235000019658 bitter taste Nutrition 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- XJSFLOJWULLJQS-NGVXBBESSA-N josamycin Chemical compound CO[C@H]1[C@H](OC(C)=O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 XJSFLOJWULLJQS-NGVXBBESSA-N 0.000 description 4
- 229960004144 josamycin Drugs 0.000 description 4
- 229960002757 midecamycin Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- -1 acetal diethylaminoacetate Chemical class 0.000 description 3
- 239000010775 animal oil Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000013530 defoamer Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- ACTOXUHEUCPTEW-BWHGAVFKSA-N 2-[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2s,5s,6r)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-o Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](O)[C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)[C@@H]1CC[C@H](N(C)C)[C@@H](C)O1 ACTOXUHEUCPTEW-BWHGAVFKSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000004187 Spiramycin Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229960003276 erythromycin Drugs 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 2
- 229950007634 kitasamycin Drugs 0.000 description 2
- XYJOGTQLTFNMQG-KJHBSLKPSA-N leucomycin V Chemical compound CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1 XYJOGTQLTFNMQG-KJHBSLKPSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 229960001294 spiramycin Drugs 0.000 description 2
- 229930191512 spiramycin Natural products 0.000 description 2
- 235000019372 spiramycin Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960004667 ethyl cellulose Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002337 glycosamines Chemical group 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4182275A JPS51118816A (en) | 1975-04-08 | 1975-04-08 | A process for stabilizing non-crystalloidal solid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1063936A true CA1063936A (en) | 1979-10-09 |
Family
ID=12618972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA249,607A Expired CA1063936A (en) | 1975-04-08 | 1976-04-05 | Preparation of amorphous solid of macrolide antibiotics |
Country Status (8)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5819844B2 (ja) * | 1978-07-13 | 1983-04-20 | 三菱自動車工業株式会社 | 機関用燃料供給装置 |
| CA1146866A (en) * | 1979-07-05 | 1983-05-24 | Yamanouchi Pharmaceutical Co. Ltd. | Process for the production of sustained release pharmaceutical composition of solid medical material |
| JPS56103109A (en) * | 1979-08-31 | 1981-08-18 | Eisai Co Ltd | Ubidecarenone-containing composition having improved dispersion properties |
| FR2525108B1 (fr) * | 1982-04-19 | 1989-05-12 | Elan Corp Ltd | Medicaments a haut degre de solubilite et procede pour leur obtention |
| US4767789A (en) * | 1986-10-21 | 1988-08-30 | American Home Products Corporation (Del.) | Spray dried acetaminophen |
| GB9713730D0 (en) * | 1997-06-30 | 1997-09-03 | Ciba Geigy Ag | Organic compounds |
| US6350786B1 (en) * | 1998-09-22 | 2002-02-26 | Hoffmann-La Roche Inc. | Stable complexes of poorly soluble compounds in ionic polymers |
-
1975
- 1975-04-08 JP JP4182275A patent/JPS51118816A/ja active Granted
-
1976
- 1976-04-05 CA CA249,607A patent/CA1063936A/en not_active Expired
- 1976-04-07 NL NL7603635A patent/NL176270C/xx not_active IP Right Cessation
- 1976-04-08 ES ES446801A patent/ES446801A1/es not_active Expired
- 1976-04-08 GB GB1423476A patent/GB1534070A/en not_active Expired
- 1976-04-08 FR FR7610280A patent/FR2306705A1/fr active Granted
- 1976-04-08 MX MX15676U patent/MX3401E/es unknown
- 1976-04-08 DE DE19762615403 patent/DE2615403C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7603635A (nl) | 1976-10-12 |
| FR2306705A1 (fr) | 1976-11-05 |
| JPS5545042B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-11-15 |
| NL176270B (nl) | 1984-10-16 |
| JPS51118816A (en) | 1976-10-19 |
| FR2306705B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-07-18 |
| DE2615403C2 (de) | 1982-07-15 |
| GB1534070A (en) | 1978-11-29 |
| NL176270C (nl) | 1985-03-18 |
| MX3401E (es) | 1980-10-30 |
| ES446801A1 (es) | 1977-06-01 |
| DE2615403A1 (de) | 1976-10-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4127647A (en) | Process for preparation of stable amorphous macrolide antibiotic solids | |
| US6346533B1 (en) | Intraconazole exhibiting an improved solubility, a method of preparing the same and a pharmaceutical composition for oral administration comprising the same | |
| US5935939A (en) | Stabilized dispersions of misoprostol | |
| US4882144A (en) | Solid, rapidly released medicament preparations containing dihydropyridines, and processes for their preparation | |
| CA2219991C (en) | Taste masking pharmaceutical composition for oral administration | |
| DE2822882C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US4835187A (en) | Spray dried ibuprofen | |
| US4665081A (en) | Solid nifedipine preparations and a process for preparing same | |
| CA1069047A (en) | Process for preparing preparations for oral administration | |
| US5739105A (en) | Cyclosporin containing composition and process for the preparation thereof | |
| CA1298199C (en) | Spray dried acetaminophen | |
| SK280194B6 (sk) | Farmaceutický prostriedok s potlačenou horkosťou | |
| GB2139892A (en) | Solid pharmaceutical preparation containing nifedipine | |
| JP2004511561A (ja) | 薬剤組成物 | |
| CA1063936A (en) | Preparation of amorphous solid of macrolide antibiotics | |
| US3962419A (en) | Stabilized antibiotic SF-837 preparation | |
| DE69419281T2 (de) | Geschmacksmaskierte feste Zubereitung und Verfahren zur Herstellung | |
| KR880004803A (ko) | 분무 건조된 아세트아미노펜 | |
| EP0088958B1 (en) | Stabilization of azulene derivatives | |
| CA2022772A1 (en) | Antibiotic composition | |
| KR800000345B1 (ko) | 마크로라이드계 항생물질의 비정질고체의 제조방법 | |
| JPS565412A (en) | Pharmaceutical composition | |
| KR100438485B1 (ko) | 아졸류 항진균제의 약제학적 조성물 | |
| KR880001558B1 (ko) | 디하이드로피리딘을 함유하는 속방출성 고형약제의 제조방법 | |
| JPS5939824A (ja) | 水溶性アズレン製剤 |