NO327138B1 - Fremgangsmate for fremstilling av flutikasonpropionat som krystallinsk polymorf form 1 - Google Patents

Fremgangsmate for fremstilling av flutikasonpropionat som krystallinsk polymorf form 1 Download PDF

Info

Publication number: NO327138B1
Authority: NO; Norway
Prior art keywords: formula; compound; fluticasone propionate; solution; solvent
Prior art date: 2002-02-04

Application number

NO20043664A

Other languages

English (en)

Norwegian (no)

Other versions

NO20043664L (no

Inventor

Steven John Coote

Rosalyn Kay Nice

Mark David Wipperman

Original Assignee

Glaxo Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-02-04

Filing date

2004-09-01

Publication date

2009-05-04

2004-09-01 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2004-09-01 Publication of NO20043664L publication Critical patent/NO20043664L/no

2009-05-04 Publication of NO327138B1 publication Critical patent/NO327138B1/no

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)

NO20043664A 2002-02-04 2004-09-01 Fremgangsmate for fremstilling av flutikasonpropionat som krystallinsk polymorf form 1 NO327138B1 (no)

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 (de)
EP (1)	EP1474436B1 (de)
JP (1)	JP2005517019A (de)
KR (1)	KR20040086331A (de)
CN (1)	CN100338087C (de)
AR (1)	AR038390A1 (de)
AT (1)	ATE446965T1 (de)
AU (1)	AU2003206836B2 (de)
BR (1)	BR0307243A (de)
CA (1)	CA2473896A1 (de)
CO (1)	CO5611115A2 (de)
DE (1)	DE60329824D1 (de)
GB (1)	GB0202564D0 (de)
IS (1)	IS7373A (de)
MX (1)	MXPA04007530A (de)
NO (1)	NO327138B1 (de)
NZ (1)	NZ534320A (de)
PL (1)	PL372214A1 (de)
RU (1)	RU2333218C2 (de)
TW (1)	TW200410982A (de)
WO (1)	WO2003066653A2 (de)
ZA (1)	ZA200405826B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
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
PT2044099E (pt) *	2006-06-14	2012-06-06	Generics Uk Ltd	Processo de preparação s-fluorometil-6,9-difluoro-11- hidroxi-16-metil-17-propioniloxi-3-oxo-androsta-l,4- dieno-17-carbotioato e seus intermediários
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
WO2012029077A2 (en) *	2010-09-01	2012-03-08	Cadila Healthcare Limited	Process for preparing fluticasone propionate/furoate
JP2014520848A (ja) *	2011-07-08	2014-08-25	ファイザー・リミテッド	１型プロピオン酸フルチカゾンの調製のための方法
CA2872845C (en)	2012-05-08	2021-11-09	Aciex Therapeutics, Inc.	Preparation of nanocrystals of fluticasone propionate
US8765725B2 (en)	2012-05-08	2014-07-01	Aciex Therapeutics, Inc.	Preparations of hydrophobic therapeutic agents, methods of manufacture and use thereof
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

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DE2455976A1 (de) *	1974-11-27	1976-08-12	Merck Patent Gmbh	Prostensaeurederivate
PH24267A (en) *	1980-02-15	1990-05-29	Glaxo Group Ltd	Androstane carbothioates and pharmaceutical compositions containing the same
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
AP1422A (en) *	2000-08-05	2005-06-05	Glaxo Group Ltd	6.Alpha.,9.alpha.-difluoro-17.alpha.-'(2-furanylcarboxyl)oxy!-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androst-1,4,-diene-17-carbothioic acid s-fluoromethyl ester as an anti-inflammatory agent.

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 US US10/502,866 patent/US20050222107A1/en not_active Abandoned
- 2003-02-03 AT AT03704541T patent/ATE446965T1/de not_active IP Right Cessation
- 2003-02-03 PL PL03372214A patent/PL372214A1/xx unknown
- 2003-02-03 AU AU2003206836A patent/AU2003206836B2/en not_active Ceased
- 2003-02-03 CA CA002473896A patent/CA2473896A1/en not_active Abandoned
- 2003-02-03 JP JP2003566024A patent/JP2005517019A/ja active Pending
- 2003-02-03 EP EP03704541A patent/EP1474436B1/de not_active Expired - Lifetime
- 2003-02-03 DE DE60329824T patent/DE60329824D1/de not_active Expired - Fee Related
- 2003-02-03 WO PCT/EP2003/001115 patent/WO2003066653A2/en active Application Filing
- 2003-02-03 CN CNB038074370A patent/CN100338087C/zh not_active Expired - Fee Related
- 2003-02-03 BR BR0307243-6A patent/BR0307243A/pt not_active IP Right Cessation
- 2003-02-03 NZ NZ534320A patent/NZ534320A/en unknown
- 2003-02-03 KR KR10-2004-7011981A patent/KR20040086331A/ko not_active Application Discontinuation
- 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
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
IS7373A (is)	2004-07-26
KR20040086331A (ko)	2004-10-08
ZA200405826B (en)	2005-08-11
AU2003206836B2 (en)	2009-01-08
CO5611115A2 (es)	2006-02-28
TW200410982A (en)	2004-07-01
BR0307243A (pt)	2004-12-14
ATE446965T1 (de)	2009-11-15
AU2003206836A1 (en)	2003-09-02
PL372214A1 (en)	2005-07-11
US20050222107A1 (en)	2005-10-06
CN100338087C (zh)	2007-09-19
WO2003066653A2 (en)	2003-08-14
AR038390A1 (es)	2005-01-12
CA2473896A1 (en)	2003-08-14
NZ534320A (en)	2007-07-27
EP1474436A2 (de)	2004-11-10
EP1474436B1 (de)	2009-10-28
MXPA04007530A (es)	2004-11-10
WO2003066653A3 (en)	2003-12-24
GB0202564D0 (en)	2002-03-20
JP2005517019A (ja)	2005-06-09
RU2333218C2 (ru)	2008-09-10
CN1642969A (zh)	2005-07-20
RU2004122928A (ru)	2005-05-27
NO20043664L (no)	2004-09-01
DE60329824D1 (de)	2009-12-10

Legal Events

Date	Code	Title	Description
2010-09-27	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
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JP2007521224A (ja)	2007-08-02	Ｒａｃ−ビカルタミドの精製及び単離方法
TW201130861A (en)	2011-09-16	Process for preparing (11β,16α)-9-fluoro-11-hydroxy-16,17-[1-methyl-ethylidenebis(oxy)]-21-[1-oxo-[4-(nitrooxymethyl)benzoxy]]pregna-1,4-dien-3,20-dione