JPS6258360B2 - - Google Patents
Info
- Publication number
- JPS6258360B2 JPS6258360B2 JP55066035A JP6603580A JPS6258360B2 JP S6258360 B2 JPS6258360 B2 JP S6258360B2 JP 55066035 A JP55066035 A JP 55066035A JP 6603580 A JP6603580 A JP 6603580A JP S6258360 B2 JPS6258360 B2 JP S6258360B2
- Authority
- JP
- Japan
- Prior art keywords
- flunisolide
- solution
- water
- alkanol
- crystallization
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 claims description 70
- 229960000676 flunisolide Drugs 0.000 claims description 67
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
- 238000002425 crystallisation Methods 0.000 claims description 14
- 230000008025 crystallization Effects 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 238000002441 X-ray diffraction Methods 0.000 claims description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000001747 exhibiting effect Effects 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 22
- 238000004458 analytical method Methods 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 238000000634 powder X-ray diffraction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000386 microscopy Methods 0.000 description 2
- 238000001907 polarising light microscopy Methods 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 238000002076 thermal analysis method Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- -1 6α-fluoro-11β Chemical compound 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003869 coulometry Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000004457 water analysis Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
-
- 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]
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)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4083079A | 1979-05-21 | 1979-05-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55154997A JPS55154997A (en) | 1980-12-02 |
| JPS6258360B2 true JPS6258360B2 (da) | 1987-12-05 |
Family
ID=21913206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6603580A Granted JPS55154997A (en) | 1979-05-21 | 1980-05-20 | Manufacture of flunisolide having peculiar crystal form |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS55154997A (da) |
| AU (1) | AU532084B2 (da) |
| BE (1) | BE883381A (da) |
| CA (1) | CA1153761A (da) |
| CH (1) | CH643567A5 (da) |
| DE (1) | DE3019250C2 (da) |
| DK (1) | DK162530C (da) |
| FR (1) | FR2457303A1 (da) |
| GB (1) | GB2052506B (da) |
| HK (1) | HK40784A (da) |
| IL (1) | IL60128A (da) |
| IT (1) | IT1133092B (da) |
| MY (1) | MY8500694A (da) |
| NL (1) | NL189201C (da) |
| NZ (1) | NZ193778A (da) |
| SE (1) | SE431549B (da) |
| SG (1) | SG37585G (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1121513B (it) * | 1979-05-28 | 1986-04-02 | Chiesi Farma Spa | Processo per la conversione di umo steroide antiinfiammatorio in una forma suscettibile di essere somministarta come aerosol |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX3864E (es) * | 1975-05-27 | 1981-08-26 | Syntex Corp | Un proceso para prepara el compuesto cristalino 6-fluiro-11b 21-dihiroxi-16 17-isopropilidendioxipregna-1 4-dien-3 20-diona |
-
1980
- 1980-05-20 JP JP6603580A patent/JPS55154997A/ja active Granted
- 1980-05-20 NZ NZ193778A patent/NZ193778A/xx unknown
- 1980-05-20 FR FR8011254A patent/FR2457303A1/fr active Granted
- 1980-05-20 AU AU58566/80A patent/AU532084B2/en not_active Expired
- 1980-05-20 IL IL60128A patent/IL60128A/xx unknown
- 1980-05-20 IT IT67791/80A patent/IT1133092B/it active Protection Beyond IP Right Term
- 1980-05-20 BE BE0/200678A patent/BE883381A/fr not_active IP Right Cessation
- 1980-05-20 GB GB8016683A patent/GB2052506B/en not_active Expired
- 1980-05-20 CH CH393980A patent/CH643567A5/de not_active IP Right Cessation
- 1980-05-20 DK DK219280A patent/DK162530C/da not_active IP Right Cessation
- 1980-05-20 DE DE3019250A patent/DE3019250C2/de not_active Expired
- 1980-05-20 NL NLAANVRAGE8002902,A patent/NL189201C/xx not_active IP Right Cessation
- 1980-05-20 SE SE8003761A patent/SE431549B/sv not_active IP Right Cessation
- 1980-05-21 CA CA000352333A patent/CA1153761A/en not_active Expired
-
1984
- 1984-05-10 HK HK407/84A patent/HK40784A/xx not_active IP Right Cessation
-
1985
- 1985-05-18 SG SG375/85A patent/SG37585G/en unknown
- 1985-12-30 MY MY694/85A patent/MY8500694A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ193778A (en) | 1982-03-16 |
| IT1133092B (it) | 1986-07-09 |
| MY8500694A (en) | 1985-12-31 |
| JPS55154997A (en) | 1980-12-02 |
| DK219280A (da) | 1980-11-22 |
| AU532084B2 (en) | 1983-09-15 |
| HK40784A (en) | 1984-05-18 |
| GB2052506B (en) | 1983-01-19 |
| NL8002902A (nl) | 1980-11-25 |
| FR2457303A1 (fr) | 1980-12-19 |
| FR2457303B1 (da) | 1983-05-13 |
| CH643567A5 (de) | 1984-06-15 |
| SG37585G (en) | 1986-01-17 |
| CA1153761A (en) | 1983-09-13 |
| AU5856680A (en) | 1980-11-27 |
| IL60128A (en) | 1984-01-31 |
| GB2052506A (en) | 1981-01-28 |
| SE431549B (sv) | 1984-02-13 |
| IL60128A0 (en) | 1980-07-31 |
| DK162530C (da) | 1992-03-30 |
| DK162530B (da) | 1991-11-11 |
| SE8003761L (sv) | 1980-11-22 |
| IT8067791A0 (it) | 1980-05-20 |
| DE3019250C2 (de) | 1982-11-11 |
| NL189201B (nl) | 1992-09-01 |
| NL189201C (nl) | 1993-02-01 |
| DE3019250A1 (de) | 1980-12-04 |
| BE883381A (fr) | 1980-11-20 |
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