SK285665B6 - Kryštalické makrolidy, spôsob ich prípravy, farmaceutický prostriedok a ich použitie - Google Patents
Kryštalické makrolidy, spôsob ich prípravy, farmaceutický prostriedok a ich použitie Download PDFInfo
- Publication number
- SK285665B6 SK285665B6 SK1866-99A SK186699A SK285665B6 SK 285665 B6 SK285665 B6 SK 285665B6 SK 186699 A SK186699 A SK 186699A SK 285665 B6 SK285665 B6 SK 285665B6
- Authority
- SK
- Slovakia
- Prior art keywords
- compound
- formula
- crystalline
- solution
- solvent
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 239000003120 macrolide antibiotic agent Substances 0.000 title description 5
- 229940041033 macrolides Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 239000013078 crystal Substances 0.000 claims abstract description 37
- 238000002425 crystallisation Methods 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims description 37
- 230000008025 crystallization Effects 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 6
- 238000010899 nucleation Methods 0.000 claims description 4
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 3
- 230000001028 anti-proliverative effect Effects 0.000 claims description 3
- 230000000947 anti-immunosuppressive effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 3
- 238000001228 spectrum Methods 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 239000006071 cream Substances 0.000 abstract description 14
- 230000001939 inductive effect Effects 0.000 abstract description 5
- 239000000839 emulsion Substances 0.000 abstract description 3
- 239000002674 ointment Substances 0.000 abstract description 3
- 230000000699 topical effect Effects 0.000 abstract description 2
- KASDHRXLYQOAKZ-OLHLVPFQSA-N pimecrolimus Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C\C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@H](Cl)[C@H](OC)C1 KASDHRXLYQOAKZ-OLHLVPFQSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000012453 solvate Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- STORWMDPIHOSMF-UHFFFAOYSA-N decanoic acid;octanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCC(O)=O.CCCCCCCCCC(O)=O STORWMDPIHOSMF-UHFFFAOYSA-N 0.000 description 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- -1 4-chloro-3- methoxycyclohexyl Chemical group 0.000 description 1
- CKOZVEHVVHCMGD-UHFFFAOYSA-N 5-[(4-fluorophenyl)methyl]-n,n-dimethyltetrazole-1-carboxamide Chemical compound CN(C)C(=O)N1N=NN=C1CC1=CC=C(F)C=C1 CKOZVEHVVHCMGD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005297 material degradation process Methods 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CFZGEMKIQUVTCC-UHFFFAOYSA-N octacos-18-ene-2,3,10,16-tetrone Chemical compound CCCCCCCCCC=CCC(=O)CCCCCC(=O)CCCCCCC(=O)C(C)=O CFZGEMKIQUVTCC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000013379 physicochemical characterization Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
-
- 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
- A61P35/00—Antineoplastic 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
-
- 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
- A61P37/02—Immunomodulators
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B7/00—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Metallurgy (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9713730.1A GB9713730D0 (en) | 1997-06-30 | 1997-06-30 | Organic compounds |
| PCT/EP1998/003929 WO1999001458A1 (en) | 1997-06-30 | 1998-06-26 | Crystalline macrolides and process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK186699A3 SK186699A3 (en) | 2000-05-16 |
| SK285665B6 true SK285665B6 (sk) | 2007-05-03 |
Family
ID=10815103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1866-99A SK285665B6 (sk) | 1997-06-30 | 1998-06-26 | Kryštalické makrolidy, spôsob ich prípravy, farmaceutický prostriedok a ich použitie |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6423722B1 (cs) |
| EP (1) | EP0994880B1 (cs) |
| JP (2) | JP3880634B2 (cs) |
| KR (1) | KR100399765B1 (cs) |
| CN (1) | CN1139595C (cs) |
| AR (1) | AR017754A1 (cs) |
| AT (1) | ATE287410T1 (cs) |
| AU (1) | AU739211B2 (cs) |
| BR (1) | BR9810956A (cs) |
| CA (1) | CA2290412C (cs) |
| CO (1) | CO4940463A1 (cs) |
| CZ (1) | CZ297244B6 (cs) |
| DE (1) | DE69828692T2 (cs) |
| DK (1) | DK0994880T3 (cs) |
| ES (1) | ES2236922T3 (cs) |
| GB (1) | GB9713730D0 (cs) |
| HU (1) | HU227755B1 (cs) |
| ID (1) | ID24897A (cs) |
| IL (1) | IL132761A0 (cs) |
| MY (1) | MY118718A (cs) |
| NO (1) | NO312765B1 (cs) |
| NZ (1) | NZ500994A (cs) |
| PE (1) | PE97699A1 (cs) |
| PL (1) | PL192761B1 (cs) |
| PT (1) | PT994880E (cs) |
| RU (1) | RU2219181C2 (cs) |
| SK (1) | SK285665B6 (cs) |
| TR (1) | TR199903189T2 (cs) |
| TW (1) | TW552264B (cs) |
| WO (1) | WO1999001458A1 (cs) |
| ZA (1) | ZA985655B (cs) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9713730D0 (en) * | 1997-06-30 | 1997-09-03 | Ciba Geigy Ag | Organic compounds |
| GB9826656D0 (en) | 1998-12-03 | 1999-01-27 | Novartis Ag | Organic compounds |
| GB0125443D0 (en) * | 2001-10-23 | 2001-12-12 | Novartis Ag | Organic Compounds |
| US7279571B2 (en) * | 2004-12-01 | 2007-10-09 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Methods of preparing pimecrolimus |
| EP1663220B1 (en) * | 2003-09-03 | 2009-12-02 | Glaxo Group Limited | Novel process for the preparation of pleuromutilin derivatives |
| PL1734927T3 (pl) * | 2004-04-08 | 2012-10-31 | Meda Pharma S A R L | Kompozycja pianki pimekrolimusa zawierająca glikol heksylenowy, ewentualnie alkohol oleilowy, dimetyloizosorbid oraz/albo triglicerydy o średniej długości łańcucha |
| US20090082386A1 (en) * | 2006-11-06 | 2009-03-26 | Erzsebet Meszarosne Sos | Ascomycin and pimecrolimus having reduced levels of desmethylascomycin and 32-deoxy-32-epichloro-desmethylascomycin respectively, and methods for preparation thereof |
| US20100105724A1 (en) * | 2006-12-07 | 2010-04-29 | Helsinn Healthcare Sa | Crystalline and amorphous forms of palonosetron hydrochloride |
| US9192697B2 (en) | 2007-07-03 | 2015-11-24 | Hemoteq Ag | Balloon catheter for treating stenosis of body passages and for preventing threatening restenosis |
| JP2012532670A (ja) | 2009-07-10 | 2012-12-20 | ボストン サイエンティフィック サイムド，インコーポレイテッド | 薬剤搬送バルーンのためのナノ結晶の使用 |
| JP5933434B2 (ja) | 2009-07-17 | 2016-06-08 | ボストン サイエンティフィック サイムド，インコーポレイテッドＢｏｓｔｏｎ Ｓｃｉｅｎｔｉｆｉｃ Ｓｃｉｍｅｄ，Ｉｎｃ． | 薬剤送達バルーンの製造方法 |
| WO2012031236A1 (en) | 2010-09-02 | 2012-03-08 | Boston Scientific Scimed, Inc. | Coating process for drug delivery balloons using heat-induced rewrap memory |
| WO2013022458A1 (en) * | 2011-08-05 | 2013-02-14 | Boston Scientific Scimed, Inc. | Methods of converting amorphous drug substance into crystalline form |
| WO2013028208A1 (en) | 2011-08-25 | 2013-02-28 | Boston Scientific Scimed, Inc. | Medical device with crystalline drug coating |
| CN108864149B (zh) | 2013-03-15 | 2022-04-05 | 生物传感器国际集团有限公司 | 雷帕霉素衍生物的纯化 |
| EP3178824A1 (en) | 2015-12-08 | 2017-06-14 | Medichem, S.A. | Process for preparing pimecrolimus |
| CA3060330A1 (en) * | 2017-05-01 | 2018-11-08 | Meda Pharma Gmbh & Co. Kg | Process to convert crude ascomycin into purified pimecrolimus |
| EP3741367A1 (en) | 2019-05-21 | 2020-11-25 | Premark Pharma GmbH | Treatment of ocular disease |
| WO2024209038A1 (en) | 2023-04-06 | 2024-10-10 | Premark Pharma Gmbh | Use of pimecrolimus for the treatment of dry eye in patients characterized by a corneal staining score of 4 or 5 on the oxford grading scale |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51118816A (en) * | 1975-04-08 | 1976-10-19 | Meiji Seika Kaisha Ltd | A process for stabilizing non-crystalloidal solid |
| US4127647A (en) * | 1975-04-08 | 1978-11-28 | Meiji Seika Kaisha, Ltd. | Process for preparation of stable amorphous macrolide antibiotic solids |
| CY1306A (en) | 1980-10-01 | 1985-12-06 | Glaxo Group Ltd | Aminoalkyl furan derivative |
| JP2728482B2 (ja) * | 1989-01-26 | 1998-03-18 | 協和醗酵工業株式会社 | マクロライド系抗生物質の精製法 |
| ES2023560A6 (es) | 1989-07-10 | 1992-01-16 | Gema Sa | Procedimiento para la produccion de hidrato de cefradina y solvato de cefradina y dimetilformamida. |
| NZ235991A (en) * | 1989-11-09 | 1993-05-26 | Sandoz Ltd | Macrolide compounds and pharmaceutical compositions thereof |
| WO1991013889A1 (en) * | 1990-03-13 | 1991-09-19 | Fisons Plc | Immunosuppressive macrocyclic compounds |
| EP0480623A1 (en) * | 1990-10-11 | 1992-04-15 | Merck & Co. Inc. | New halomacrolides and derivatives having immunosuppressive activity |
| US5143918A (en) * | 1990-10-11 | 1992-09-01 | Merck & Co., Inc. | Halomacrolides and derivatives having immunosuppressive activity |
| DE69217762T2 (de) | 1991-07-30 | 1997-10-09 | Ajinomoto Kk | Kristalle von N-(Trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanin und Verfahren zu ihrer Herstellung |
| US5247076A (en) | 1991-09-09 | 1993-09-21 | Merck & Co., Inc. | Imidazolidyl macrolides having immunosuppressive activity |
| US5221740A (en) | 1992-01-16 | 1993-06-22 | American Home Products Corporation | Oxepane isomers of rapamycin useful as immunosuppressive agents |
| UA41884C2 (uk) * | 1993-11-05 | 2001-10-15 | Амерікан Хоум Продактс Корпорейшн | Спосіб відокремлення рапаміцину від кислотних, основних та неполярних нейтральних домішок, присутніх в концентраті екстрактів ферментаційного бульйону або маточних розчинів |
| US5626757A (en) * | 1994-02-22 | 1997-05-06 | Advanced Separation Technologies Inc. | Macrocyclic antibiotics as separation agents |
| JPH11512096A (ja) * | 1995-08-24 | 1999-10-19 | メルク エンド カンパニー インコーポレーテッド | イミダゾリルマクロライド免疫抑制剤の製造方法 |
| GB9713730D0 (en) * | 1997-06-30 | 1997-09-03 | Ciba Geigy Ag | Organic compounds |
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1997
- 1997-06-30 GB GBGB9713730.1A patent/GB9713730D0/en active Pending
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1998
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- 1998-06-26 SK SK1866-99A patent/SK285665B6/sk not_active IP Right Cessation
- 1998-06-26 RU RU2000101826/04A patent/RU2219181C2/ru active
- 1998-06-26 JP JP50628799A patent/JP3880634B2/ja not_active Expired - Lifetime
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- 1998-06-26 BR BR9810956-1A patent/BR9810956A/pt not_active Application Discontinuation
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| PC4A | Assignment and transfer of rights |
Owner name: MEDA PHARMA S.A.R.L., LUXEMBOURG, LU Free format text: FORMER OWNER: NOVARTIS AG, BASEL, CH Effective date: 20130222 |
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| MK4A | Expiry of patent |
Expiry date: 20180626 |