NO327138B1 - Fremgangsmate for fremstilling av flutikasonpropionat som krystallinsk polymorf form 1 - Google Patents
Fremgangsmate for fremstilling av flutikasonpropionat som krystallinsk polymorf form 1 Download PDFInfo
- Publication number
- NO327138B1 NO327138B1 NO20043664A NO20043664A NO327138B1 NO 327138 B1 NO327138 B1 NO 327138B1 NO 20043664 A NO20043664 A NO 20043664A NO 20043664 A NO20043664 A NO 20043664A NO 327138 B1 NO327138 B1 NO 327138B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- fluticasone propionate
- solution
- solvent
- Prior art date
Links
- 229960000289 fluticasone propionate Drugs 0.000 title claims description 43
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 title claims description 43
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 95
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 64
- 239000002904 solvent Substances 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical group CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000007788 liquid Substances 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 24
- 239000012296 anti-solvent Substances 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 150000002460 imidazoles Chemical class 0.000 claims description 13
- 239000010410 layer Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 7
- 239000003444 phase transfer catalyst Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 5
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 135
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 239000002253 acid Substances 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000000725 suspension Substances 0.000 description 21
- 239000002002 slurry Substances 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 238000000634 powder X-ray diffraction Methods 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 9
- 230000008901 benefit Effects 0.000 description 9
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 9
- 238000002955 isolation Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 8
- 238000007614 solvation Methods 0.000 description 8
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 7
- LHMHCLYDBQOYTO-UHFFFAOYSA-N bromofluoromethane Chemical compound FCBr LHMHCLYDBQOYTO-UHFFFAOYSA-N 0.000 description 7
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- -1 pentan-3-one Chemical compound 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 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 2
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 2
- UDYGXWPMSJPFDG-UHFFFAOYSA-M benzyl(tributyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 UDYGXWPMSJPFDG-UHFFFAOYSA-M 0.000 description 2
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 2
- 239000012455 biphasic mixture Substances 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011872 intimate mixture Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 1
- 206010027654 Allergic conditions Diseases 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 101100482220 Sulfurisphaera tokodaii (strain DSM 16993 / JCM 10545 / NBRC 100140 / 7) triC gene Proteins 0.000 description 1
- 241000394605 Viola striata Species 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- YKOQQFDCCBKROY-UHFFFAOYSA-N n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)CC YKOQQFDCCBKROY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- 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
- A61P11/06—Antiasthmatics
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0202564.1A GB0202564D0 (en) | 2002-02-04 | 2002-02-04 | Process |
| PCT/EP2003/001115 WO2003066653A2 (en) | 2002-02-04 | 2003-02-03 | Process for the production of fluticasone propionate, in particular of polymorphic form 1 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20043664L NO20043664L (no) | 2004-09-01 |
| NO327138B1 true NO327138B1 (no) | 2009-05-04 |
Family
ID=9930366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20043664A NO327138B1 (no) | 2002-02-04 | 2004-09-01 | Fremgangsmate for fremstilling av flutikasonpropionat som krystallinsk polymorf form 1 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US20050222107A1 (es) |
| EP (1) | EP1474436B1 (es) |
| JP (1) | JP2005517019A (es) |
| KR (1) | KR20040086331A (es) |
| CN (1) | CN100338087C (es) |
| AR (1) | AR038390A1 (es) |
| AT (1) | ATE446965T1 (es) |
| AU (1) | AU2003206836B2 (es) |
| BR (1) | BR0307243A (es) |
| CA (1) | CA2473896A1 (es) |
| CO (1) | CO5611115A2 (es) |
| DE (1) | DE60329824D1 (es) |
| GB (1) | GB0202564D0 (es) |
| IS (1) | IS7373A (es) |
| MX (1) | MXPA04007530A (es) |
| NO (1) | NO327138B1 (es) |
| NZ (1) | NZ534320A (es) |
| PL (1) | PL372214A1 (es) |
| RU (1) | RU2333218C2 (es) |
| TW (1) | TW200410982A (es) |
| WO (1) | WO2003066653A2 (es) |
| ZA (1) | ZA200405826B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL153462A0 (en) * | 2002-12-16 | 2003-07-06 | Chemagis Ltd | Thiocarboxylic acid organic salts and processes utilizing the same |
| AU2013202835B2 (en) * | 2006-06-14 | 2015-11-12 | Generics [Uk] Limited | Process for the preparation of S-fluoromethyl-6,9-difluoro-11-hydroxy-16-methyl-17-propionyloxy-3-oxo-androsta-1, 4-diene-17-carbothioate and intermediates |
| EP2044099B1 (en) * | 2006-06-14 | 2012-05-23 | Generics [UK] Limited | Process for the preparation of s-fluoromethyl-6 ,9 -difluoro-11 -hydroxy-16 -methyl-17 -propionyloxy-3-oxo-androsta-1,4-diene-17 -carbothioate and intermediates |
| WO2012029077A2 (en) * | 2010-09-01 | 2012-03-08 | Cadila Healthcare Limited | Process for preparing fluticasone propionate/furoate |
| EP2729480A4 (en) * | 2011-07-08 | 2014-12-31 | Pfizer Ltd | PROCESS FOR THE PREPARATION OF FLUTICASONE PROPIONATE, FORM 1 |
| US8765725B2 (en) | 2012-05-08 | 2014-07-01 | Aciex Therapeutics, Inc. | Preparations of hydrophobic therapeutic agents, methods of manufacture and use thereof |
| PT3517541T (pt) | 2012-05-08 | 2020-08-28 | Nicox Ophthalmics Inc | Forma polimórfica de propionato de fluticasona |
| DE102012221219B4 (de) * | 2012-11-20 | 2014-05-28 | Jesalis Pharma Gmbh | Verfahren zur Vergrößerung der Partikelgröße kristalliner Wirkstoff-Mikropartikel |
| US9815865B2 (en) | 2013-01-07 | 2017-11-14 | Nicox Ophthalmics, Inc. | Preparations of hydrophobic therapeutic agents, methods of manufacture and use thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2455976A1 (de) * | 1974-11-27 | 1976-08-12 | Merck Patent Gmbh | Prostensaeurederivate |
| CA1201114A (en) * | 1980-02-15 | 1986-02-25 | Gordon H. Phillipps | Androstane carbothioates |
| US5783677A (en) * | 1993-09-24 | 1998-07-21 | Procter & Gamble Pharmaceuticals, Inc. | Deoxy and oxygen-substituted sugar-containing 14-aminosteroid compounds |
| US5488188A (en) * | 1994-09-29 | 1996-01-30 | Merrell Dow Pharmaceuticals Inc. | Process for the preparation of (E)-1-amino-2-(fluoromethylene)-4-(p-fluorophenyl)butane, novel processes for preparing an intermediate thereof, and novel intermediates thereof |
| GB9622173D0 (en) * | 1996-10-24 | 1996-12-18 | Glaxo Group Ltd | Particulate Products |
| GB9925934D0 (en) * | 1999-11-03 | 1999-12-29 | Glaxo Group Ltd | Novel apparatus and process |
| AR032471A1 (es) * | 2000-08-05 | 2003-11-12 | Glaxo Group Ltd | Derivado de androstano y solvatos del mismo, su uso para la fabricacion de medicamentos, composiciones farmaceuticas que los comprenden, procesos para preparar tales derivados, intermediarios utiles en la preparacion de tales derivados, procesos para preparar tales intermediarios, y compuestos inter |
-
2002
- 2002-02-04 GB GBGB0202564.1A patent/GB0202564D0/en not_active Ceased
-
2003
- 2003-01-30 TW TW092102249A patent/TW200410982A/zh unknown
- 2003-01-31 AR ARP030100299A patent/AR038390A1/es not_active Application Discontinuation
- 2003-02-03 AT AT03704541T patent/ATE446965T1/de not_active IP Right Cessation
- 2003-02-03 RU RU2004122928/04A patent/RU2333218C2/ru not_active IP Right Cessation
- 2003-02-03 MX MXPA04007530A patent/MXPA04007530A/es active IP Right Grant
- 2003-02-03 KR KR10-2004-7011981A patent/KR20040086331A/ko not_active Application Discontinuation
- 2003-02-03 EP EP03704541A patent/EP1474436B1/en not_active Expired - Lifetime
- 2003-02-03 DE DE60329824T patent/DE60329824D1/de not_active Expired - Fee Related
- 2003-02-03 NZ NZ534320A patent/NZ534320A/en unknown
- 2003-02-03 BR BR0307243-6A patent/BR0307243A/pt not_active IP Right Cessation
- 2003-02-03 JP JP2003566024A patent/JP2005517019A/ja active Pending
- 2003-02-03 PL PL03372214A patent/PL372214A1/xx unknown
- 2003-02-03 CA CA002473896A patent/CA2473896A1/en not_active Abandoned
- 2003-02-03 AU AU2003206836A patent/AU2003206836B2/en not_active Ceased
- 2003-02-03 CN CNB038074370A patent/CN100338087C/zh not_active Expired - Fee Related
- 2003-02-03 WO PCT/EP2003/001115 patent/WO2003066653A2/en active Application Filing
- 2003-02-03 US US10/502,866 patent/US20050222107A1/en not_active Abandoned
-
2004
- 2004-07-21 ZA ZA200405826A patent/ZA200405826B/en unknown
- 2004-07-26 IS IS7373A patent/IS7373A/is unknown
- 2004-07-30 CO CO04074014A patent/CO5611115A2/es not_active Application Discontinuation
- 2004-09-01 NO NO20043664A patent/NO327138B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200405826B (en) | 2005-08-11 |
| AU2003206836B2 (en) | 2009-01-08 |
| NZ534320A (en) | 2007-07-27 |
| AR038390A1 (es) | 2005-01-12 |
| RU2004122928A (ru) | 2005-05-27 |
| PL372214A1 (en) | 2005-07-11 |
| BR0307243A (pt) | 2004-12-14 |
| DE60329824D1 (de) | 2009-12-10 |
| NO20043664L (no) | 2004-09-01 |
| KR20040086331A (ko) | 2004-10-08 |
| CO5611115A2 (es) | 2006-02-28 |
| IS7373A (is) | 2004-07-26 |
| EP1474436B1 (en) | 2009-10-28 |
| CA2473896A1 (en) | 2003-08-14 |
| MXPA04007530A (es) | 2004-11-10 |
| CN1642969A (zh) | 2005-07-20 |
| CN100338087C (zh) | 2007-09-19 |
| ATE446965T1 (de) | 2009-11-15 |
| RU2333218C2 (ru) | 2008-09-10 |
| AU2003206836A1 (en) | 2003-09-02 |
| WO2003066653A2 (en) | 2003-08-14 |
| WO2003066653A3 (en) | 2003-12-24 |
| TW200410982A (en) | 2004-07-01 |
| JP2005517019A (ja) | 2005-06-09 |
| GB0202564D0 (en) | 2002-03-20 |
| EP1474436A2 (en) | 2004-11-10 |
| US20050222107A1 (en) | 2005-10-06 |
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