CZ281318B6 - Monohydrát mometasonfuroátu, způsob přípravy této látky a přípravy lékových kompozic z ní - Google Patents
Monohydrát mometasonfuroátu, způsob přípravy této látky a přípravy lékových kompozic z ní Download PDFInfo
- Publication number
- CZ281318B6 CZ281318B6 CZ93383A CZ38393A CZ281318B6 CZ 281318 B6 CZ281318 B6 CZ 281318B6 CZ 93383 A CZ93383 A CZ 93383A CZ 38393 A CZ38393 A CZ 38393A CZ 281318 B6 CZ281318 B6 CZ 281318B6
- Authority
- CZ
- Czechia
- Prior art keywords
- monohydrate
- alpha
- furoate
- dione
- dichloro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 150000004682 monohydrates Chemical class 0.000 title claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 title description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 239000012047 saturated solution Substances 0.000 claims abstract description 6
- 238000002425 crystallisation Methods 0.000 claims abstract description 5
- 230000008025 crystallization Effects 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229960004123 mometasone furoate monohydrate Drugs 0.000 abstract description 23
- 239000003814 drug Substances 0.000 abstract description 6
- 229940079593 drug Drugs 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- 238000003756 stirring Methods 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 229960002744 mometasone furoate Drugs 0.000 description 14
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 13
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 239000008213 purified water Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 8
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 8
- 229920000053 polysorbate 80 Polymers 0.000 description 8
- 229940068968 polysorbate 80 Drugs 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000001509 sodium citrate Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 239000002253 acid Substances 0.000 description 3
- 229960000686 benzalkonium chloride Drugs 0.000 description 3
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000004302 potassium sorbate Substances 0.000 description 3
- 229940069338 potassium sorbate Drugs 0.000 description 3
- 235000010241 potassium sorbate Nutrition 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 244000248349 Citrus limon Species 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 238000002447 crystallographic data Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- -1 furoate monohydrate Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229910002483 Cu Ka Inorganic materials 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 101100355632 Rattus norvegicus Ran gene Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000002547 anomalous effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000958 atom scattering Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229960001716 benzalkonium Drugs 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 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 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0043—Nose
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58023990A | 1990-09-10 | 1990-09-10 | |
| PCT/US1991/006249 WO1992004365A1 (en) | 1990-09-10 | 1991-09-06 | Mometasone furoate monohydrate, process for making same and pharmaceutical compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ38393A3 CZ38393A3 (en) | 1994-01-19 |
| CZ281318B6 true CZ281318B6 (cs) | 1996-08-14 |
Family
ID=24320279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ93383A CZ281318B6 (cs) | 1990-09-10 | 1991-09-06 | Monohydrát mometasonfuroátu, způsob přípravy této látky a přípravy lékových kompozic z ní |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US6180781B1 (OSRAM) |
| EP (1) | EP0548114B1 (OSRAM) |
| JP (1) | JPH0725789B2 (OSRAM) |
| KR (1) | KR960013445B1 (OSRAM) |
| CN (1) | CN1030920C (OSRAM) |
| AT (1) | ATE113604T1 (OSRAM) |
| AU (1) | AU663471B2 (OSRAM) |
| BG (1) | BG60755B2 (OSRAM) |
| CA (1) | CA2091360C (OSRAM) |
| CZ (1) | CZ281318B6 (OSRAM) |
| DE (2) | DE69104991T2 (OSRAM) |
| DK (1) | DK0548114T5 (OSRAM) |
| EE (1) | EE02962B1 (OSRAM) |
| ES (1) | ES2065701T3 (OSRAM) |
| FI (1) | FI111078B (OSRAM) |
| HK (1) | HK185996A (OSRAM) |
| HR (1) | HRP920383B1 (OSRAM) |
| HU (1) | HU213401B (OSRAM) |
| IE (1) | IE67056B1 (OSRAM) |
| IL (1) | IL99437A (OSRAM) |
| LU (1) | LU90366I2 (OSRAM) |
| MX (2) | MX9203396A (OSRAM) |
| MY (1) | MY106644A (OSRAM) |
| NL (1) | NL980012I2 (OSRAM) |
| NO (1) | NO300548B1 (OSRAM) |
| NZ (1) | NZ239711A (OSRAM) |
| OA (1) | OA09772A (OSRAM) |
| PH (1) | PH30443A (OSRAM) |
| PL (1) | PL165803B1 (OSRAM) |
| PT (1) | PT98905B (OSRAM) |
| SI (1) | SI9111497A (OSRAM) |
| TW (2) | TW229208B (OSRAM) |
| WO (1) | WO1992004365A1 (OSRAM) |
| YU (1) | YU48666B (OSRAM) |
| ZA (1) | ZA917148B (OSRAM) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0548114T5 (da) * | 1990-09-10 | 1995-01-30 | Schering Corp | Mometason-furoat-monohydrat, fremgangsmåde til fremtilling deraf og farmaceutiske præparater indeholdende dette |
| US5837699A (en) * | 1994-01-27 | 1998-11-17 | Schering Corporation | Use of mometasone furoate for treating upper airway passage diseases |
| PE44995A1 (es) | 1994-01-27 | 1995-12-18 | Schering Corp | Furoato de mometasona para el tratamiento de las enfermedades pulmonares y de las vias respiratorias |
| US5886200A (en) * | 1996-07-01 | 1999-03-23 | Schering Corporation | Process for the preparation of 17-esters of 9 α, 21-dihalo-pregnane-11 β, 17 α-diol-20-ones |
| US5976573A (en) | 1996-07-03 | 1999-11-02 | Rorer Pharmaceutical Products Inc. | Aqueous-based pharmaceutical composition |
| CN1059476C (zh) * | 1996-08-21 | 2000-12-13 | 邓维鹏 | 金黄色铝合金硒盐电解着色方法 |
| US6187765B1 (en) * | 1997-10-09 | 2001-02-13 | Schering Corporation | Mometasone furoate suspensions for nebulization |
| DE69804998T2 (de) * | 1997-10-09 | 2002-12-12 | Schering Corp., Kenilworth | Mometasonfuroat-suspensionen zum zerstäuben |
| MY133181A (en) * | 1998-09-10 | 2007-10-31 | Schering Corp | Methods and compositions for treating sinusitis, otitis media and other related disorders using antihistamines |
| ES2246234T3 (es) | 1999-05-04 | 2006-02-16 | Strakan International Limited | Glicosidos de androgenos y actividad androgenica de los mismos. |
| GB0207906D0 (en) * | 2002-04-05 | 2002-05-15 | 3M Innovative Properties Co | Formoterol and mometasone aerosol formulations |
| US7811606B2 (en) | 2003-04-16 | 2010-10-12 | Dey, L.P. | Nasal pharmaceutical formulations and methods of using the same |
| US8912174B2 (en) * | 2003-04-16 | 2014-12-16 | Mylan Pharmaceuticals Inc. | Formulations and methods for treating rhinosinusitis |
| US9808471B2 (en) | 2003-04-16 | 2017-11-07 | Mylan Specialty Lp | Nasal pharmaceutical formulations and methods of using the same |
| JP2007504123A (ja) * | 2003-08-29 | 2007-03-01 | ランバクシー ラボラトリーズ リミテッド | Ｉｖ型ホスホジエステラーゼの阻害剤 |
| EP1694655A2 (en) * | 2003-11-26 | 2006-08-30 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| US7491725B2 (en) | 2004-02-06 | 2009-02-17 | Bristol-Myers Squibb Company | Process for preparing 2-aminothiazole-5-aromatic carboxamides as kinase inhibitors |
| EP1934219A1 (en) | 2005-09-16 | 2008-06-25 | Ranbaxy Laboratories Limited | Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors |
| US20070099883A1 (en) * | 2005-10-07 | 2007-05-03 | Cheryl Lynn Calis | Anhydrous mometasone furoate formulation |
| JP2009512676A (ja) | 2005-10-19 | 2009-03-26 | ランバクシー ラボラトリーズ リミテッド | ムスカリン性受容体アンタゴニストの医薬組成物 |
| US20090054382A1 (en) * | 2005-10-19 | 2009-02-26 | Abhijit Ray | Compositions of phosphodiesterase type iv inhibitors |
| CN100389121C (zh) * | 2005-12-09 | 2008-05-21 | 天津药业集团有限公司 | 糠酸莫美他松中间体21-羟的制备方法 |
| CN100436473C (zh) * | 2005-12-09 | 2008-11-26 | 天津药业集团有限公司 | 糠酸莫美他松中间体21-酯及制法 |
| DE102006034883A1 (de) * | 2006-07-25 | 2008-01-31 | Hermal Kurt Herrmann Gmbh & Co. Ohg | Pharmazeutische Zusammensetzung enthaltend Mometasonfuroat |
| WO2008035316A2 (en) * | 2006-09-22 | 2008-03-27 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| US20110021473A1 (en) * | 2006-09-22 | 2011-01-27 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type-iv |
| US20080207659A1 (en) * | 2007-02-15 | 2008-08-28 | Asit Kumar Chakraborti | Inhibitors of phosphodiesterase type 4 |
| WO2008111009A1 (en) * | 2007-03-14 | 2008-09-18 | Ranbaxy Laboratories Limited | Pyrazolo [3, 4-b] pyridine derivatives as phosphodiesterase inhibitors |
| ES2382715T3 (es) | 2007-03-14 | 2012-06-12 | Ranbaxy Laboratories Limited | Derivados de pirazol[3,4-B]piridina como inhibidores de fosfodiesterasa |
| EP2111861A1 (en) | 2008-04-21 | 2009-10-28 | Ranbaxy Laboratories Limited | Compositions of phosphodiesterase type IV inhibitors |
| ES2592536T3 (es) | 2009-05-29 | 2016-11-30 | Pearl Therapeutics, Inc. | Composiciones para administración a los pulmones de antagonistas muscarínicos de acción prolongada y agonistas de los receptores beta-2-adrenérgicos de acción prolongada y métodos y sistemas asociados |
| US8815258B2 (en) * | 2009-05-29 | 2014-08-26 | Pearl Therapeutics, Inc. | Compositions, methods and systems for respiratory delivery of two or more active agents |
| PT105058B (pt) | 2010-04-21 | 2013-04-17 | Hovione Farmaciencia S A | Processo para processamento de partículas de ingredientes activos farmacêuticos |
| KR102391332B1 (ko) | 2013-03-15 | 2022-04-26 | 펄 테라퓨틱스 인코포레이티드 | 미립자 결정질 재료를 컨디셔닝하는 방법 및 시스템 |
| CN107260671B (zh) * | 2016-04-08 | 2021-03-26 | 天津金耀集团有限公司 | 一种糠酸莫米松混悬鼻喷剂组合物 |
| CN107266518B (zh) * | 2016-04-08 | 2021-03-30 | 天津金耀集团有限公司 | 一种糠酸莫米松晶型及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE8790T1 (de) * | 1981-02-02 | 1984-08-15 | Schering Corporation | Aromatische heterocyclische steroidester, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen, die sie enthalten. |
| US4783444A (en) | 1984-09-17 | 1988-11-08 | Schering Corporation | Antiglaucoma compositions and methods |
| US4808610A (en) * | 1986-10-02 | 1989-02-28 | Schering Corporation | Mometasone furoate anti-inflammatory cream composition using hexylene glycol |
| US4775529A (en) * | 1987-05-21 | 1988-10-04 | Schering Corporation | Steroid lotion |
| DK0548114T5 (da) * | 1990-09-10 | 1995-01-30 | Schering Corp | Mometason-furoat-monohydrat, fremgangsmåde til fremtilling deraf og farmaceutiske præparater indeholdende dette |
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| IF00 | In force as of 2000-06-30 in czech republic | ||
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Effective date: 20110906 |