PL157145B1 - Method for manufacturing crystalline shitomycin dihydrate - Google Patents
Method for manufacturing crystalline shitomycin dihydrateInfo
- Publication number
- PL157145B1 PL157145B1 PL1988273590A PL27359088A PL157145B1 PL 157145 B1 PL157145 B1 PL 157145B1 PL 1988273590 A PL1988273590 A PL 1988273590A PL 27359088 A PL27359088 A PL 27359088A PL 157145 B1 PL157145 B1 PL 157145B1
- Authority
- PL
- Poland
- Prior art keywords
- dihydrate
- azithromycin
- water
- water content
- shitomycin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 150000004683 dihydrates Chemical class 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 20
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[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 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 claims abstract description 18
- 229960004099 azithromycin Drugs 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 10
- VQEMDSRIOVZAOM-UHFFFAOYSA-N 4-(4-methylsulfonylphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CSC(N)=N1 VQEMDSRIOVZAOM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229960004924 azithromycin dihydrate Drugs 0.000 claims abstract description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 30
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 150000004682 monohydrates Chemical class 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 238000009835 boiling Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229960003276 erythromycin Drugs 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- 229930006677 Erythromycin A Natural products 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 208000035143 Bacterial infection Diseases 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- HRKNNHYKWGYTEN-HOQMJRDDSA-N (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)NC[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 HRKNNHYKWGYTEN-HOQMJRDDSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Molecular Biology (AREA)
- Cardiology (AREA)
- Biotechnology (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1987/001612 WO1989000576A1 (en) | 1987-07-09 | 1987-07-09 | Azithromycin dihydrate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL273590A1 PL273590A1 (en) | 1989-03-20 |
| PL157145B1 true PL157145B1 (en) | 1992-04-30 |
Family
ID=22202456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1988273590A PL157145B1 (en) | 1987-07-09 | 1988-07-07 | Method for manufacturing crystalline shitomycin dihydrate |
Country Status (45)
Families Citing this family (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20020231A2 (en) * | 2002-03-18 | 2003-12-31 | Pliva D D | ISOSTRUCTURAL PSEUDOPOLYMORPHS OF 9-DEOXO-9a-AZA-9a-METHYL-9a-HOMOERYTHROMYCIN A |
| US5912331A (en) * | 1991-03-15 | 1999-06-15 | Merck & Co., Inc. | Process for the preparation of 9-deoxo-9(Z)-hydroxyiminoerythromycin A |
| US5985844A (en) * | 1992-03-26 | 1999-11-16 | Merck & Co., Inc. | Homoerythromycin A derivatives modified at the 4"-and 8A-positions |
| US5189159A (en) * | 1992-04-02 | 1993-02-23 | Merck & Co., Inc. | 8a-AZA-8a-homoerythromycin cyclic iminoethers |
| EP0539223A1 (en) * | 1991-10-25 | 1993-04-28 | Ono Pharmaceutical Co., Ltd. | Glycine derivative monosodium salt tetrahydrate having an inhibitory effect on elastase |
| US5215980A (en) * | 1992-01-17 | 1993-06-01 | Merck & Co., Inc. | 10-AZA-9-deoxo-11-deoxy-erythromycin A and derivatives thereof |
| US5210235A (en) * | 1992-08-26 | 1993-05-11 | Merck & Co., Inc. | Methods of elaborating erythromycin fragments into amine-containing fragments of azalide antibiotics |
| US5332807A (en) * | 1993-04-14 | 1994-07-26 | Merck & Co., Inc. | Process of producing 8A- and 9A-azalide antibiotics |
| CN1034734C (zh) * | 1993-12-10 | 1997-04-30 | 北京市集才药物研究所 | 一种新的阿齐红霉素结晶及其制备方法 |
| US5605889A (en) | 1994-04-29 | 1997-02-25 | Pfizer Inc. | Method of administering azithromycin |
| RO114740B1 (ro) * | 1994-05-06 | 1999-07-30 | Pfizer | Compozitie cu eliberare controlata, procedeu de obtinere a acesteia si metoda de tratament |
| ES2122905B1 (es) * | 1996-07-11 | 1999-11-16 | Astur Pharma Sa | Sintesis de 11,12-hidrogenoortoborato de 9-desoxo-9a-aza-11,12-desoxi-9a-metil-9a-homoeritromicina a. un procedimiento para la preparacion de 9-desoxo-9a-aza-9a-metil-9a-homoeritromicina a dihidrato (azitromicina dihidrato). |
| RU2220148C2 (ru) * | 1997-10-16 | 2003-12-27 | Плива, Фармацойтска Индустрия, Дионичко Друштво | Производные азитромицина и способ их получения |
| US6861411B1 (en) | 1997-12-02 | 2005-03-01 | Pfizer, Inc. | Method of treating eye infections with azithromycin |
| PT102130A (pt) * | 1998-03-13 | 1999-09-30 | Hovione Sociedade Quimica S A | Processo de preparacao de dihidrato de azitromicina |
| TW546302B (en) * | 1998-05-08 | 2003-08-11 | Biochemie Sa | Improvements in macrolide production |
| CA2245398C (en) * | 1998-08-21 | 2002-01-29 | Apotex Inc. | Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof |
| EP1484062A1 (en) * | 1998-11-30 | 2004-12-08 | Teva Pharmaceutical Industries Limited | Crystalline azithromycin, process for manufacture and pharmaceutical compositions thereof |
| US7056893B2 (en) | 1999-03-31 | 2006-06-06 | Insite Vision, Inc. | Topical treatment for prevention of ocular infections |
| US6239113B1 (en) | 1999-03-31 | 2001-05-29 | Insite Vision, Incorporated | Topical treatment or prevention of ocular infections |
| HUP0201341A3 (en) * | 1999-05-18 | 2003-03-28 | Pfizer Prod Inc | Novel crystalline forms of a macrolide antibiotic, process for its preparation and pharmaceutical compositions containing it |
| US6703372B1 (en) | 1999-06-29 | 2004-03-09 | Biochemie S.A. | Macrolides |
| ES2177373B1 (es) | 1999-11-26 | 2003-11-01 | Astur Pharma Sa | Preparacion de azitromicina en su forma no cristalina |
| ATE388159T1 (de) * | 2000-01-04 | 2008-03-15 | Teva Pharma | Verfahren zur herstellung von azithromycin- dihydrat |
| ES2162764B1 (es) * | 2000-05-17 | 2003-04-01 | Ercros Ind Sa | Forma polimorfica del dihidrato de azitromicina, y su procedimiento deobtencion. |
| ATE320441T1 (de) | 2000-07-25 | 2006-04-15 | Silanes Sa De Cv Lab | Einstufiges verfahren zur herstellung von 7,16- |
| ES2172417B1 (es) * | 2000-07-31 | 2003-09-16 | Sint Quimica Sa | Nueva forma mejorada de azitromicina monohidrato de menor higroscopicidad, procedimiento de preparacion y composiciones farmaceuticas que la comprenden. |
| JP2004506664A (ja) * | 2000-08-23 | 2004-03-04 | ウォックハート・リミテッド | 無水アジトロマイシンの製造法 |
| RU2279439C2 (ru) * | 2000-11-27 | 2006-07-10 | Сандоз Аг | Азитромицин в форме моногидрата и способ его получения |
| KR100815163B1 (ko) * | 2000-11-27 | 2008-03-19 | 바이오케미 에스.에이. | 마크로라이드 용매화물 |
| IN190080B (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) * | 2001-01-29 | 2003-06-07 | Alembic Ltd | |
| KR100491183B1 (ko) * | 2001-03-21 | 2005-05-25 | 한미약품 주식회사 | 아지트로마이신의 제조방법 및 이 방법에 사용되는9-데옥소-9에이-아자-9에이-호모에리트로마이신 에이의결정성 수화물 |
| ATE319730T1 (de) | 2001-05-22 | 2006-03-15 | Pfizer Prod Inc | Neue kristallforme von azithromycin |
| EP1671979B1 (en) | 2001-05-22 | 2008-08-13 | Pfizer Products Inc. | New Cristal Form of Azithromycin |
| US6861413B2 (en) | 2001-05-22 | 2005-03-01 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
| MXPA04001605A (es) * | 2001-08-21 | 2004-07-08 | Pfizer Prod Inc | Azitromicina en una sola dosis para tratar infecciones respiratorias. |
| CN1606433A (zh) * | 2001-12-21 | 2005-04-13 | 辉瑞产品公司 | 阿齐霉素湿法制粒法 |
| JP2005513099A (ja) * | 2001-12-21 | 2005-05-12 | ファイザー・プロダクツ・インク | アジスロマイシンの直接的に圧縮可能な配合品 |
| AU2003201146B2 (en) * | 2002-02-01 | 2008-04-17 | Pfizer Products Inc. | Dry granulated formulations of azithromycin |
| US7376064B2 (en) | 2002-02-25 | 2008-05-20 | Samsung Electronics Co., Ltd. | Method and apparatus for recording data on optical recording medium |
| ITMI20021209A1 (it) * | 2002-06-04 | 2003-12-04 | Chemi Spa | Processo di preparazione di azitromicina ad elevata purezza |
| US6855813B2 (en) * | 2002-07-19 | 2005-02-15 | Alembic Limited | Process for the preparation of azithromycin monohydrate |
| HRP20020614A2 (en) | 2002-07-22 | 2004-06-30 | PLIVA-ISTRAŽIVAČKI INSTITUT d.o.o. | Rhombic pseudopolymorph of 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin a |
| GB2395482A (en) * | 2003-07-03 | 2004-05-26 | Jubilant Organosys Ltd | Process for preparing non-hygroscopic azithromycin dihydrate |
| US20050013835A1 (en) * | 2003-07-15 | 2005-01-20 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
| ATE399536T1 (de) * | 2003-12-04 | 2008-07-15 | Pfizer Prod Inc | Verfahren zur herstellung von pharmazeutischen multiteilchenförmigen produkten |
| CN1889931A (zh) * | 2003-12-04 | 2007-01-03 | 辉瑞产品公司 | 利用挤压器制备优选含泊洛沙姆和甘油酯的多重粒子阿奇霉素组合物的喷雾－冻凝方法 |
| WO2005053652A1 (en) | 2003-12-04 | 2005-06-16 | Pfizer Products Inc. | Multiparticulate crystalline drug compositions containing a poloxamer and a glyceride |
| WO2005053639A2 (en) * | 2003-12-04 | 2005-06-16 | Pfizer Products Inc. | Controlled release multiparticulates formed with dissolution enhancers |
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-
1987
- 1987-07-09 RO RO143593A patent/RO107257B1/ro unknown
- 1987-07-09 RU SU874742955A patent/RU2066324C1/ru active
- 1987-07-09 UA UA93004522A patent/UA27040C2/uk unknown
- 1987-07-09 MX MX1221388A patent/MX12213A/es unknown
- 1987-07-09 WO PCT/US1987/001612 patent/WO1989000576A1/en active IP Right Grant
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1988
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- 1988-06-15 AP APAP/P/1988/000093A patent/AP44A/en active
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- 1988-07-06 JP JP63168637A patent/JPH0631300B2/ja not_active Expired - Lifetime
- 1988-07-06 CS CS884896A patent/CS272241B2/cs not_active IP Right Cessation
- 1988-07-07 CA CA000571381A patent/CA1314876C/en not_active Expired - Lifetime
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- 1988-07-07 EG EG376/88A patent/EG18527A/xx active
- 1988-07-07 AR AR88311356A patent/AR243532A1/es active
- 1988-07-07 PL PL1988273590A patent/PL157145B1/pl unknown
- 1988-07-07 PH PH37189A patent/PH30953A/en unknown
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- 1988-07-07 PT PT87933A patent/PT87933B/pt not_active IP Right Cessation
- 1988-07-08 ZA ZA884925A patent/ZA884925B/xx unknown
- 1988-07-08 OA OA59384A patent/OA08743A/xx unknown
- 1988-07-08 SI SI8811325A patent/SI8811325A8/sl unknown
- 1988-07-08 NZ NZ225338A patent/NZ225338A/xx unknown
- 1988-07-08 DK DK198803806A patent/DK172573B1/da not_active IP Right Cessation
- 1988-07-08 AU AU18839/88A patent/AU604553B2/en not_active Expired
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- 1988-07-08 CN CN88104331A patent/CN1016785B/zh not_active Expired
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1990
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1992
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1993
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1994
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1995
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1998
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